Diethyl Ether → (1R,2S)-2-(tert-butyldimethylsilyloxy)-1-(2-fluoro-3-(trifluoromethyl)phenyl)propan-1-ol

HRID 2279469ノート

反応式

HRID 2279469 の反応式
[Si:1]([O:8][C@@H:9]([CH3:23])[C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[C:13]=1[F:22])=[O:11])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].CCOCC>[BH4-].[Zn+2].[BH4-].O>[Si:1]([O:8][C@@H:9]([CH3:23])[C@@H:10]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:19])([F:21])[F:20])[C:13]=1[F:22])[OH:11])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

参加物

5

反応物 2

HCID 3283Diethyl EtherHCID 86705481(S)-2-(tert-butyldimethylsilyloxy)-1-(2-fluoro-3-(trifluoromethyl)phenyl)propan-1-one

生成物 1

HCID 86705482(1R,2S)-2-(tert-butyldimethylsilyloxy)-1-(2-fluoro-3-(trifluoromethyl)phenyl)propan-1-ol

試薬・触媒・溶媒 2

HCID 12838295ZINC;boranuide触媒HCID 962Water溶媒

実験手順

To a solution of 112 (1.374 g, 3.921 mmol) and Et2O (20 mL) cooled to 0° C. was added a solution of zinc borohydride (8.46 mL, 1.176 mmol) was added and the reaction was stirred for 2 h. Water was added slowly and the mixture was extracted with ether. The organic layer was washed with water and brine then dried, filtered, and concentrated to afford (1R,2S)-2-(tert-butyldimethylsilyloxy)-1-(2-fluoro-3-(trifluoromethyl)phenyl)propan-1-ol (114) which was used without additional purification.

後処理

  1. additionwas added
  2. extractionthe mixture was extracted with ether
  3. washThe organic layer was washed with water and brine
  4. customthen dried
  5. filtrationfiltered
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-94ec11e52c684e60bb22c716627683e3
出典データセット
uspto-grants-2015_09
特許番号
US09133187B2

反応ノート

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