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CAS No. : | 129150-68-1 | MDL No. : | MFCD24448669 |
Formula : | C13H19NO3 | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | OWIZBOBVXITREP-UHFFFAOYSA-N |
M.W : | 237.30 | Pubchem ID : | 11031911 |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | |
Hazard Statements: | H302-H315-H319 | Packing Group: | |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With hydrogen;palladium 10% on activated carbon; In ethanol; under 2068.65 Torr; | Step B [2-(3-Hydroxy-phenyl)-ethyl]-carbamic acid tert-butyl ester; 1 g of Pd/C 10% was added to a solution of 13 g (0.039 mol) of [2-(3-benzyloxy-phenyl)- ethyl]-carbamic acid tert-butyl ester in 100 ml of ethanol. The mixture was hydrogenated at 40 psi overnight. The catalyst was filtered off and washed with ethanol. The solvent was removed under vacuum and 9.4 g of the title compound were obtained as a colourless oil in quantitative yield.1H-NMR CDCl3: 7.22-7.12 (m, IH); 6.78-6.66 (m, 3H); 4.56 (bs, IH); 3.42-3.30 (m, 2H); 2.74 (t, 2H); 1.44 (S, 9H). |
98% | With palladium on activated charcoal; hydrogen; In methanol; at 20℃;Inert atmosphere; | A round-bottomed flask fitted with stir bar was charged with tert-butyl {2-[3- (benzyloxy)phenyl]ethyl}carbamate (Intermediate 68; 1 .43g, 0.OO4mol)in MeOH (5OmL) The flask was filled with Argon, and then Pd/C (143mg, O.OOlmol) was added employing an Argon cone stream to avoid solvent ignition. The flask was coupled with a quick-fit T-adaptor with one outlet to the hydrogen balloon and the other to the vacuum line. The flask was emptied by connecting it to the vacuum and then filled with hydrogen. This op-eration was repeated twice. The reaction mixture was stirred overnight at room tempera-ture. The solid was filtered through a Celite pad and concentrated under reduced pressure to give the title compound as a white solid (980mg, 98%).LRMS (m/z): 238 (M+1)+ |
With hydrogen;palladium 10% on activated carbon; In methanol; at 20℃;Product distribution / selectivity; | To a solution of Intermediate 54 (1.4 g, 4.37 mmol) in methanol (50 ml_) was added palladium on charcoal (10%, 0.143 g). The reaction mixture was hydrogenated under a balloon pressure at room temperature overnight. The catalyst was filtered through Celite and the solvent removed under reduced pressure to give the title compound as a solid, which was used in the next step without further purification. MS (M+): 238. |
With hydrogen;palladium 10% on activated carbon; In methanol; under 1810.07 Torr; for 16h; | The 2-(3-Benzyloxyphenyl)-(tert-butoxycarbonyl)ethylamine obtained in Step 1 and 10% Pd/C (1.3 g) in MeOH (240 ml), was hydrogenated in a Parr apparatus for 16 h at 35 psi. The catalyst was removed by filtration on Celite pad and the solvent was evaporated under reduced pressure. The crude oil was used without further purification.1H NMR (300 MHz, CDCl3): delta 7.19 (dd, J=7.8 Hz, J=7.8 Hz, J=7.8 Hz, 1H), 6.82-6.66 (m, 3H), 4.56 (bs, 1H), 3.39 (dt, J=7.0 Hz, J=6.3 Hz, 2H), 2.76 (t, J=7.0 Hz, 2H), 1.46 (s, 9H). ESI+MS: calcd for C13H19NO3: 237.30; found: 238.2 (MH+). | |
With hydrogen;palladium 10% on activated carbon; In methanol; under 1810.07 Torr; for 16h; | The 2-(3-Benzyloxyphenyl)-(tert-butoxycarbonyl)ethylamine obtained in Step 1 and 10% Pd/C (1.3 g) in MeOH (240 ml), was hydrogenated in a Parr apparatus for 16h at 35 psi. The catalyst was removed by filtration on Celite pad and the solvent was evaporated under reduced pressure. The crude oil was used without further purification.1H NMR (300 MHz, CDCl3): delta 7.19 (dd, J = 7.8 Hz, J = 7.8 Hz, IH), 6.82 - 6.66 (m, 3H), 4.56 (bs, IH), 3.39 (dt, J = 7.0 Hz, J = 6.3 Hz, 2H), 2.76 (t, J = 7.0 Hz, 2H), 1.46 (s, 9H). ESI+MS: calcd for C13Hi9NO3: 237.30; found: 238.2 (MH+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58.6% | With potassium carbonate; In water; at 23℃; for 24h; | General procedure: Serotonin creatinine sulfate monohydrate (1.0 equiv, 18.8 mmol) orthe appropriate scaffold was dissolved in H2O (80 mL). Potassiumcarbonate (2.0 equiv, 37.6 mmol) was added all at once and reaction was stirredwith a dry stir bar. Di-tert-butyl dicarbonate (1.0 equiv, 18.8 mmol) was addedall at once via syringe and reaction was stirred for 24 hours at 23C exposedto the atmosphere (no argon). The product was then extracted with 3x10 mL EtOAcand then washed with 20 mL of H2O, 20 mL of 5% HCl, and 20 mL of brine.The organic portion was then filtered through MgSO4 and solvent wasevaporated off under reduced pressure, leaving a sticky green solid. |
With potassium carbonate; In 1,4-dioxane; water; at 0 - 20℃; for 1.5h;Product distribution / selectivity; | Obtained from Intermediate 28 (11 g, 80.2 mmol), potassium carbonate (23.1 g) and di-tert-butyl dicarbonate (11.2 g, 51.3 mmol) by the same procedure described in Intermediate 20. The title compound was obtained as a solid (10.8 g) and used in the next step without further purification. MS (M+): 238. | |
In tetrahydrofuran; water; at 20℃; for 16h; | A 33% solution of HBr in acetic acid (150 ml) was cooled to 0 C. and 3-methoxy phenethylamine (10.0 g, 66.0 mmol) was added portionwise. The mixture was heated to 80 C. and stirred for 16 h. The solvent was evaporated under reduced pressure and the residue was dissolved in water (160 ml). 4 M NaOH (15 ml) was added followed by 2 M of NaOH (130 ml). A solution of boc2O (15.8 g, 72.6 mmol) in THF (160 ml) was added dropwise and the mixture was stirred at room temperature for 16 h. The upper organic layer of the resulting mixture was separated and the aqueous layer was extracted with CH2Cl2 (3×100 ml). The combined organic solutions were dried over Na2SO4, filtered and the solvent was evaporated under reduced pressure. The crude title compound (16.8 g) was obtained as a brown gum that was used in the following steps without further purification.ESI+MS: calcd for C13H19NO3: 237.3; found: 182.1 (MH+-t-butyl, major fragment). |
With triethylamine; In tetrahydrofuran; at 20℃;Cooling with ice; | A solution of 2-(3-hydroxyphenyl)ethylamine (5.15 g, 29.7 mmol) in THF (65 mL) was treated with Et3N (9.30 mL, 2.2 equiv) and cooled on an ice-water bath. Di-tert-butyldicarbonate (6.80 g, 31.1 mmol) was added and the cooling bath was removed. After approx. 0.5 h THF (35 mL) and Et3N (5.0 mL) were added to improve solubility. After stirring overnight, the reaction mixture was diluted with EtOAc, washed with water and satd aq NaCl solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was dissolved in acetone (100 mL) and treated with benzyl bromide (3.90 mL, 33 mmol) and K2CO3 (4.50 g, 33 mmol). The reaction mixture was heated at 50 C for 19 h. The solvent was removed under reduced pressure. The residue was partitioned between CH2Cl2 and 2 M aq NaOH. The organic layer was washed with satd aq NaCl solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The crude product, containing a small amount of residual benzyl bromide, was deprotected using general procedure 5 to give 2-(3-benzyloxyphenyl)ethylamine hydrochloride as a white solid, 5.49 g. | |
With triethylamine; In tetrahydrofuran; for 0.5h;Cooling with ice; | Cyclopenta[2,3]pyrrolo[2,1-a]isoquinoline-3-nitromethyl, 1,2,3,3a,4,5,7,8-octahydro-10-benzyloxy-2-methyl-5-oxo-(2S,3R,3aS,12bR) A solution of 2-(3-hydroxyphenyl)ethyl amine (5.15 g, 29.7 mmol) in THF (65 mL) was treated with Et3N (9.3 mL, 2.2 eq.) and cooled on an ice-water bath. Di-t-butyldicarbonate (6.8 g, 31.1 mmol) was added and the cooling bath was removed. After approx. 0.5 h, THF (35 mL) and Et3N (5 mL) were added to improve solubility. After stirring o.n., the reaction mixture was diluted with EtOAc, washed with water and sat. aq. NaCl solution, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was dissolved in acetone (100 mL) and treated with benzyl bromide (3.9 mL, 33 mmol) and K2CO3 (4.5 g, 33 mmol). The reaction mixture was heated at 50 C. for 19 h. The solvent was removed under reduced pressure. The residue was partitioned between dichloromethane and 2 M aq. NaOH. The organic layer was washed with sat. aq. NaCl solution, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude product, containing a small amount of residual benzyl bromide, was deprotected by treatment with p-dioxane (20 mL) and 4 M HCl in dioxane (50 mL) at r.t. for 2 h. The reaction mixture was diluted with Et2O and the solid precipitate was filtered off, washed with Et2O and dried to give 2-(3-benzyloxyphenyl)ethyl amine hydrochloride as a white solid, 5.49 g. HPLC-(Method A)-tr=2.85 min. (94%). 1H-NMR (300 MHz, DMSO-d6): delta=8.04 (broad s, 3H, NH3+), 7.34-7.42 (m, 4H), 7.22 (t, J=7.7 Hz, 1H), 6.80-6.91 (m, 3H), 5.07 (s, 2H, PhCH2O), 3.00 (m, 2H), 2.81-2.85 (m, 2H). |
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