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CAS No. : | 4276-09-9 | MDL No. : | MFCD00064297 |
Formula : | C5H13NO | Boiling Point : | No data available |
Linear Structure Formula : | H2NCH(CH(CH3)2)CH2OH | InChI Key : | NWYYWIJOWOLJNR-YFKPBYRVSA-N |
M.W : | 103.16 | Pubchem ID : | 6950587 |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P264-P271-P280-P302+P352-P304+P340+P312-P305+P351+P338-P332+P313-P337+P313-P403+P233-P405-P501 | 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 |
---|---|---|
Example 73A (2R)-2-[(6-bromo-3-fluoropyridin-2-yl)methyl]amino}-3-methylbutan-1-ol <strong>[885267-36-7]6-bromo-3-fluoropicolinaldehyde</strong> (4.0 g, 19.61 mmol) and (R)-2-amino-3-methylbutan-1-ol (2.281 mL, 20.59 mmol) were dissolved in methanol (100 mL) and stirred at ambient temperature for 1 hour and 15 minutes. Sodium borohydride (0.742 g, 19.61 mmol) was added and the mixture was stirred for another 1 hour and 30 minutes. The volume of the reaction mixture was reduced, and the mixture was quenched with 200 mL 1.0 N NaOH, and extracted with 200 mL dichloromethane (2*). The organic phase was extracted with 1.0 N HCl and partitioned. The aqueous phase was separated, neutralized with 3.0 N NaOH, extracted with EtOAc, organic phase separated and washed with brine. The organic phase was dried over Na2SO4, filtered, and concentrated to obtain the title compound as an orange solid. MS (ESI+) m/z 291.0 (M+H); 1H NMR (300 MHz, DMSO-d6) delta 7.69 (t, J=8.8, 1H), 7.60 (dd, J=8.6, 3.7, 1H), 4.42 (t, J=5.2, 1H), 3.92-3.75 (m, 2H), 3.43 (dt, J=10.7, 4.8, 1H), 2.34-2.24 (m, 1H), 2.08 (s, 1H), 1.87-1.71 (m, 1H), 0.83 (dd, J=8.5, 6.9, 6H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
470.1 mg | A cooled (0C) suspension of 37a (1 .36 g, 8.434 mmol) and magnesium sulfate (5 g) in dichloromethane (40 ml.) was treated with D-valinol (870.0 mg, 8.434 mmol). After stirring at 0C to RT for 23 h, the mixture was filtered and the volatiles were removed in vacuo. The residue was dissolved in anhydrous dichloromethane (40 ml.) and was subsequently treated with triethylamine (1 .3 ml_, 9.277 mmol) and a solution of trimethylsilyl chloride (9.3 ml_, 9.277 mmol, 1 M in dichloromethane). After stirring at RT for 24 h, the volatiles were removed in vacuo and the residue was triturated with diethyl ether//'so-hexane (100 ml_, 1 :1 ). The white solid was filtered off and the filtrate was evaporated to dryness to provide the intermediate imine. In a cooled (-40C) 3-neck round-bottom flask, equipped with a nitrogen line and an addition funnel was introduced anhydrous diethyl ether (25 ml.) and a solution of /so-propyl lithium (29 ml_, 20.242 mmol, 0.7 M in pentane). To this mixture, a solution of the imine in anhydrous diethyl ether (25 ml.) was added dropwise over 15 min. After stirring at -40C for 2.5 h, the reaction was quenched with hydrochloric acid (2 M, 50 ml.) and the mixture was allowed to warm to RT. The acidic aqueous layer was basified with NaOH pellets at 0C and then extracted with diethyl ether (2 x). The organics were combined, dried over sodium sulfate, filtered and the volatiles were removed in vacuo. The residue was purified by silica gel chromatography using a 50 g Isolute cartridge eluted with a continuous gradient of /'so-hexanes/ethyl acetate 1 :0 to 1 :1 to afford the title compound (470.1 mg, 19% over 3 steps) as a colorless oil |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
470.1 mg | A cooled (0 C.) suspension of 37a (1.36 g, 8.434 mmol) and magnesium sulfate (5 g) in dichloromethane (40 mL) was treated with D-valinol (870.0 mg, 8.434 mmol). After stirring at 0 C. to RT for 23 h, the mixture was filtered and the volatiles were removed in vacuo. The residue was dissolved in anhydrous dichloromethane (40 mL) and was subsequently treated with triethylamine (1.3 mL, 9.277 mmol) and a solution of trimethylsilyl chloride (9.3 mL, 9.277 mmol, 1 M in dichloromethane). After stirring at RT for 24 h, the volatiles were removed in vacuo and the residue was triturated with diethyl ether/iso-hexane (100 mL, 1:1). The white solid was filtered off and the filtrate was evaporated to dryness to provide the intermediate imine. In a cooled (-40 C.) 3-neck round-bottom flask, equipped with a nitrogen line and an addition funnel was introduced anhydrous diethyl ether (25 mL) and a solution of iso-propyllithium (29 mL, 20.242 mmol, 0.7 M in pentane). To this mixture, a solution of the imine in anhydrous diethyl ether (25 mL) was added dropwise over 15 min. After stirring at -40 C. for 2.5 h, the reaction was quenched with hydrochloric acid (2 M, 50 mL) and the mixture was allowed to warm to RT. The acidic aqueous layer was basified with NaOH pellets at 0 C. and then extracted with diethyl ether (2×). The organics were combined, dried over sodium sulfate, filtered and the volatiles were removed in vacuo. The residue was purified by silica gel chromatography using a 50 g Isolute cartridge eluted with a continuous gradient of iso-hexanes/ ethyl acetate 1:0 to 1:1 to afford the title compound (470.1 mg, 19% over 3 steps) as a colorless oil. |
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