Methanol → (2S)-2-(2,3,4-Trifluoroanilino)propanol

HRID 8462

반응식

HRID 8462 반응식
[BH4-].[Na+].[F:3][C:4]1[C:16]([F:17])=[C:15]([F:18])[CH:14]=[CH:13][C:5]=1[NH:6][C@@H:7]([CH3:12])[C:8](OC)=[O:9].CO.O>C(OC)(C)(C)C>[F:3][C:4]1[C:16]([F:17])=[C:15]([F:18])[CH:14]=[CH:13][C:5]=1[NH:6][C@@H:7]([CH3:12])[CH2:8][OH:9]

참가 물질

6

반응물 4

HCID 887MethanolHCID 962WaterHCID 4311764Sodium borohydrideHCID 10125210Methyl (2S)-2-(2,3,4-trifluoroanilino)propionate

생성물 1

HCID 11401466(2S)-2-(2,3,4-Trifluoroanilino)propanol

시약·촉매·용매 1

HCID 15413tert-Butyl methyl ether용매2회

실험 절차

At room temperature, sodium borohydride (35.7 mg) was suspended in methyl t-butyl ether (0.2 ml). Then a solution (0.8 ml) of methyl (2S)-2-(2,3,4-trifluoroanilino)propionate (200 mg, 99.8% ee) in methyl t-butyl ether was added to the solution. After adding methanol (137.4 mg), the liquid reaction mixture was stirred for 1 hour. Then water was added to the liquid reaction mixture followed by extraction with ethyl acetate. The organic layer was washed with water and a saturated aqueous solution of ammonium chloride and dried over anhydrous magnesium sulfate. After evaporating the solvent, the obtained residue was subjected to silica gel column chromatography to thereby give 176 mg (99.8% ee) of the title compound as an oily substance. The 1H-NMR and IR spectral data of this product was identical with those of the compound obtained in Example 51.

후처리

  1. customAt room temperature
  2. customthe liquid reaction mixture
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materiala saturated aqueous solution of ammonium chloride and dried over anhydrous magnesium sulfate
  6. customAfter evaporating the solvent

출처 및 근거

ORD 기록
ord-df8c448ae5194ed18654920404b87f55
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07087778B2

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