Acetic Acid → 4-[(S)-1-(4-Bromo-phenyl)-ethylamino]-1-methoxy-2-phenyl-butan-2-ol
반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([NH2:10])[CH3:9])=[CH:4][CH:3]=1.C(O)(=O)C.[OH:15][C:16]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([CH2:20][O:21][CH3:22])[CH2:17][CH:18]=O>O1CCCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([NH:10][CH2:18][CH2:17][C:16]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)([OH:15])[CH2:20][O:21][CH3:22])[CH3:9])=[CH:4][CH:3]=1참가 물질
실험 절차
(S)-1-(4-Bromo-phenyl)-ethylamine (0.93 g), NaB(OAc)3 (0.98 g), and acetic acid (0.27 mL) were added in the given order to a solution of 3-hydroxy-4-methoxy-3-phenyl-butyraldehyde (0.90 g) in tetrahydrofuran (20 mL) at ca. 10-15° C. The cooling bath was removed and the mixture was stirred at room temperature for 2 h. Then, water (50 mL) and 1 M aqueous NaOH solution (20 mL) were added and the resulting mixture was stirred for another 30 min. The mixture was extracted with ethyl acetate and the combined extracts were washed with water and brine. After drying (MgSO4), the solvent was removed to give the title compound which was submitted to the subsequent reaction step without further purification. Yield: 1.80 g (quantitative). Mass spectrum (ESI+): m/z=378/380 (Br) [M+H]+
후처리
- customThe cooling bath was removed
- additionThen, water (50 mL) and 1 M aqueous NaOH solution (20 mL) were added
- stirringthe resulting mixture was stirred for another 30 min
- extractionThe mixture was extracted with ethyl acetate
- washthe combined extracts were washed with water and brine
- dry with materialAfter drying (MgSO4)
- customthe solvent was removed
출처 및 근거
- ORD 기록
- ord-1c209d81b068442eab848c615b4312c5
- 출처 데이터셋
- uspto-grants-2013_10
- 특허 번호
- US08569292B2
반응 노트
불러오는 중…