4-Benzyl-2-methyl-6-(trifluoromethyl)morpholin-3-one → 4-Benzyl-cis-2-methyl-6-(trifluoromethyl)morpholine
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[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:7]([N:14]1[CH2:19][CH:18]([C:20]([F:23])([F:22])[F:21])[O:17][CH:16]([CH3:24])[C:15]1=O)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>>[CH2:7]([N:14]1[CH2:19][C@H:18]([C:20]([F:23])([F:21])[F:22])[O:17][C@H:16]([CH3:24])[CH2:15]1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1참가 물질
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- 온도
- 60 °C
실험 절차
Dry LiAlH4 (797 mg, 21 mmol, Aldrich) is suspended in dry, inhibitor free THF (15 ml) and treated with a solution of 4-benzyl-2-methyl-6-(trifluoromethyl)morpholin-3-one (2.73 g, 10 mmol) in dry, inhibitor free THF (15 ml). The mixture is heated to 60° C. with stirring for 30 minutes. The mixture is diluted with MTBE (25 mL) and quenched sequentially with H2O (0.8 mL), 6.0 M NaOH (0.8 mL) and H2O (2.4 mL). The white slurry is filtered and the inorganic salts were washed with MTBE (200 mL). The solvent is removed by rotary evaporation and the product is purified in 3 portions on Biotage Flash 40M+ cartridges using a 10 minute linear gradient of 3% -10% MTBE in heptane. The products are combined and dried under high vacuum yielding a colorless oil.
후처리
- customin dry
- customin dry
- additionThe mixture is diluted with MTBE (25 mL)
- customquenched sequentially with H2O (0.8 mL), 6.0 M NaOH (0.8 mL) and H2O (2.4 mL)
- filtrationThe white slurry is filtered
- washthe inorganic salts were washed with MTBE (200 mL)
- customThe solvent is removed by rotary evaporation
- customthe product is purified in 3 portions on Biotage Flash 40M+ cartridges
- waitusing a 10 minute linear gradient of 3% -10% MTBE in heptane
- customdried under high vacuum
- customyielding a colorless oil
출처 및 근거
- ORD 기록
- ord-d5f38d0dbb4f47dbb75b6e50fe5cac6d
- 출처 데이터셋
- uspto-grants-2009_10
- 특허 번호
- US07605157B2
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