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CAS No. : | 177947-96-5 | MDL No. : | MFCD06656142 |
Formula : | C9H15NO3 | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | JVQOZRRUGOADSU-UHFFFAOYSA-N |
M.W : | 185.22 | Pubchem ID : | 10726182 |
Synonyms : |
|
Chemical Name : | tert-Butyl 3-formylazetidine-1-carboxylate |
Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | |
Hazard Statements: | H315-H319-H335 | 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 |
---|---|---|
A solution of n-BuLi (2.0 mL, 5 mmol, 2.5 M solution in hexane) was slowly added to a solution of <strong>[24134-09-6]5-bromo-1,2-dimethyl-1H-imidazole</strong> (0.88 g, 5.1 mmol) in THF (35 mL) at -78 C. After addition, stirring was continued for an additional 30 minutes and tert-butyl 3-formylazetidine-1-carboxylate (0.94 g, 5.1 mmol) dissolved in THF (12 mL) was slowly added. An additional 4 mL of THF was used to complete the quantitative addition. The mixture was stirred at -78 C. for 5 minutes then warmed to room temperature and stirred for 1 hour. The solution was quenched with aqueous saturated NH4Cl solution and layers were separated. The aqueous layer was extracted with EtOAc and the combined organic extracts washed with brine, dried over MgSO4, filtered and evaporated in vacuo. The crude product was purified by triturating with DCM to provide the title compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
57% | Step 1: tert-butyl 3-[(trans-2-phenylcyclopropyl)amino]methyl}azetidine-1-carboxylate To a solution of tert-butyl 3-formylazetidine-1-carboxylate (556 mg, 3.00 mmol, Alfa Aesar: CatNo. H52794) and 2-phenylcyclopropanamine hydrochloride (600. mg, 3.54 mmol, trans, racemic, J&W PharmLab: CatNo.20-0073S, Lot: JW152-128A) in DCM (10 mL) was added acetic acid (510 muL, 9.0 mmol). The resulting yellow solution was stirred at room temperature overnight then Na(OAc)3BH (1.9 g, 9.0 mmol) was added. The reaction mixture was stirred at room temperature for 1 h then diluted with DCM, washed with saturated Na2CO3, water and brine. The organic layer was dried over Na2SO4 then concentrated. The residue was purified on silica gel column eluting with 0 to 100% EtOAc/Hexanes to give the desired product (513 mg, 57%) as a light yellow oil. LC-MS calculated for C14Hi9N2O2 (M-tBu+2H)+: m/z=247.1; found 247.2. | |
57% | Step 1: tert-butyl 3-[(trans-2-phenylcyclopropyl)amino]methyl}azetidine-1-carboxylate To the solution of tert-butyl 3-formylazetidine-1-carboxylate (556 mg, 3.00 mmol, Alfa Aesar: Cat No.H52794) and 2-phenylcyclopropanamine hydrochloride (600. mg, 3.54 mmol, trans, racemic, J&W PharmLab: Cat No.20-0073S, Lot: JW152-128A) in DCM (10 mL) was added acetic acid (510 muL, 9.0 mmol). The resulting yellow solution was stirred at room temperature overnight then Na(OAc)3BH (1.9 g, 9.0 mmol) was added. The reaction mixture was stirred at room temperature for 1 h then diluted with DCM, washed with saturated Na2CO3, water and brine. The organic layer was dried over Na2SO4 then concentrated. The residue was purified on silica gel column eluting with 0 to 100% EtOAc/Hexanes to give the desired product (513 mg, 57%) as a light yellow oil. LC-MS calculated for C14H19N2O2 (M-tBu+2H)+: m/z=247.1; found 247.2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | With diisobutylaluminium hydride; In dichloromethane; at -78 - 0℃; for 0.5h;Inert atmosphere; | Compound 41 (1.00 g, 5.30 mmol)Soluble in dichloromethane,Add to the three-necked bottle under Ar protection,After cooling to -78 C,DIBAL-H (11.7 mL, 11.7 mmol) was slowly added dropwise, and the addition was completed.After stirring at the same temperature for 30 min, slowly rise to 0 C.Stop the reaction by adding 2 mL of anhydrous methanol.200 mL of 10% aqueous citric acid solution was added. At this point, a white solid precipitated.Keep the temperature until the white solid disappears. Extracted 3 times with dichloromethane, dried, and concentrated the crude product by column chromatography (PE: EA=5:1)A colorless slightly viscous liquid compound 42 (0.57 g, 3.24 mmol),The yield was 61%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
6.55 g | To a solution of <strong>[38573-88-5]2,3-difluorobromobenzene</strong> (10.0 g, 51.8 mmol) in dry diethyl ether (120 ml), under nitrogen at -78°C, was added drop wise , n-hexyllithium (2.3 M in hexane, 22.5 ml, 51 .8 mmol). The mixture was stirred for 10 mm after which a solution of tert-butyl 3-formylazetidine-i- carboxylate (12.2 g, 49.2 mmol) in dry diethyl ether (30 ml) was added drop wise. The resultingmixture was stirred at -78°C for 0.5 h and then brought to ambient temperature and stirred for 1 h. Water (50 ml) was added and the mixture was extracted with ethyl acetate (2x50 ml). The combined organic phase was washed with brine, dried (Mg504), filtered and evaporated to dryness. The crude product was purified by flash column chromatography on silica gel (ethyl acetate/isooctane, 0:1 to i:i)to give the title compound (6.55 g). MS mlz (rel. intensity, 70 eV)299 (M+, 2), 244 (36), 225 (29), 153(99), 57 (bp). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | The mixture of 2-methyl-l,8-naphthyridine (115 mg, 0.799 mmol), E6A (148 mg, 0.799 mmol), and 4-methylbenzenesulfonamide (137 mg, 0.799 mmol) in DME (10 mL) was heated at 170 °C under microwave conditions for 2 h. The mixture was purified by preparative HPLC (Phenomenex Luna Axia 5mu Omicron18 30 chi 100 mm; 10 min gradient from 85percent A: 15percent B to 0percent A: 100percent B (A = 90percent H2O/10 percent ACN + 0.1percent TFA); (B = 90percent ACN/10percent H2O + 0.1percent TFA); detection at 220 nm) to yield E6B (170 mg, 68percent yield). LCMS (ES): m/z 312.2 [M+H]+. |
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