Water → (S)-2-{2-methyl-4-[2,2,2-trifluoro-1-(4-methoxy-benzyloxy)-1-trifluoromethyl-ethyl]-phenoxy}-3-phenyl-propan-1-ol

HRID 1452699ノート

反応式

HRID 1452699 の反応式
C([O:8][C:9](=O)[C@@H:10]([O:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]([O:34][CH2:35][C:36]2[CH:41]=[CH:40][C:39]([O:42][CH3:43])=[CH:38][CH:37]=2)([C:30]([F:33])([F:32])[F:31])[C:26]([F:29])([F:28])[F:27])=[CH:21][C:20]=1[CH3:44])[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)C1C=CC=CC=1.[BH4-].[Na+].O>CO.C1COCC1>[CH3:44][C:20]1[CH:21]=[C:22]([C:25]([O:34][CH2:35][C:36]2[CH:37]=[CH:38][C:39]([O:42][CH3:43])=[CH:40][CH:41]=2)([C:26]([F:27])([F:28])[F:29])[C:30]([F:32])([F:33])[F:31])[CH:23]=[CH:24][C:19]=1[O:18][C@@H:10]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:9][OH:8]

参加物

6

反応物 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 86604228(S)-2-{2-methyl-4-[2,2,2-trifluoro-1-(4-methoxy-benzyloxy)-1-trifluoromethyl-ethyl]-phenoxy}-3-phenyl-propionic acid benzyl ester

生成物 1

HCID 86604230(S)-2-{2-methyl-4-[2,2,2-trifluoro-1-(4-methoxy-benzyloxy)-1-trifluoromethyl-ethyl]-phenoxy}-3-phenyl-propan-1-ol収率 68%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

1.7 g (2.7 mmol) of (S)-2-{2-methyl-4-[2,2,2-trifluoro-1-(4-methoxy-benzyloxy)-1-trifluoromethyl-ethyl]-phenoxy}-3-phenyl-propionic acid benzyl ester was dissolved in a mixture of 11 mL of methanol and 11 mL of THF and cooled to 0° C. To this solution 1.0 g (26.9 mmol) of NaBH4 were added in portions, and the mixture was slowly warmed to room temperature overnight. Water was added, the phases were separated and the inorganic one was extracted with dichloromethane. The combined organic phases were washed with brine, dried (Na2SO4), filtered and evaporated. Purification by column chromatography with CH2Cl2/MeOH 95:5 yielded 960 mg (68%) (S)-2-{2-methyl-4-[2,2,2-trifluoro-1-(4-methoxy-benzyloxy)-1-trifluoromethyl-ethyl]-phenoxy}-3-phenyl-propan-1-ol as a light yellow oil, MS: 528 (M)+.

後処理

  1. temperaturethe mixture was slowly warmed to room temperature overnight
  2. customthe phases were separated
  3. extractionthe inorganic one was extracted with dichloromethane
  4. washThe combined organic phases were washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated
  8. customPurification by column chromatography with CH2Cl2/MeOH 95:5

出典と根拠

ORDレコード
ord-aaee2b92ed6249229a79e69c4e5e3a3b
出典データセット
uspto-grants-2009_01
特許番号
US07473705B2

反応ノート

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