4-Benzyl-2-methyl-6-(trifluoromethyl)morpholin-3-one → 4-Benzyl-cis-2-methyl-6-(trifluoromethyl)morpholine

HRID 1966322ノート

反応式

HRID 1966322 の反応式
[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]=1

参加物

3

反応物 2

HCID 184555914-Benzyl-2-methyl-6-(trifluoromethyl)morpholin-3-oneHCID 21226445Aluminium lithium hydride

生成物 1

HCID 588470294-Benzyl-cis-2-methyl-6-(trifluoromethyl)morpholine

反応条件

温度
60 °C

実験手順

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), 6.0M 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.

後処理

  1. customin dry
  2. customin dry
  3. additionThe mixture is diluted with MTBE (25 mL)
  4. customquenched sequentially with H2O (0.8 mL), 6.0M NaOH (0.8 mL) and H2O (2.4 mL)
  5. filtrationThe white slurry is filtered
  6. washthe inorganic salts were washed with MTBE (200 mL)
  7. customThe solvent is removed by rotary evaporation
  8. customthe product is purified in 3 portions on Biotage Flash 40M+ cartridges
  9. waitusing a 10 minute linear gradient of 3%-10% MTBE in heptane
  10. customdried under high vacuum
  11. customyielding a colorless oil

出典と根拠

ORDレコード
ord-c31886624fc84ab7926dc26a541edec3
出典データセット
uspto-grants-2013_04
特許番号
US08420646B2

反応ノート

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