Ammonium Chloride → 2-{Hydroxy[4-(trifluoromethyl)phenyl]methyl}cyclopropanecarbonitrile

HRID 561484노트

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HRID 561484 반응식
[BH4-].[Na+].[F:3][C:4]([F:19])([F:18])[C:5]1[CH:17]=[CH:16][C:8]([C:9]([CH:11]2[CH2:13][CH:12]2[C:14]#[N:15])=[O:10])=[CH:7][CH:6]=1.[Cl-].[NH4+]>C(O)C.C(OCC)(=O)C>[OH:10][CH:9]([C:8]1[CH:7]=[CH:6][C:5]([C:4]([F:3])([F:18])[F:19])=[CH:17][CH:16]=1)[CH:11]1[CH2:13][CH:12]1[C:14]#[N:15]

참가 물질

6

반응물 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 583920932-[4-(Trifluoromethyl)benzoyl]cyclopropanecarbonitrile

생성물 1

HCID 583924082-{Hydroxy[4-(trifluoromethyl)phenyl]methyl}cyclopropanecarbonitrile

시약·촉매·용매 2

HCID 702Ethanol용매HCID 8857Ethyl Acetate용매2회

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온도
40 °C

실험 절차

298 mg (7.88 mmol) of sodium borohydride were added to 1.71 g (7.17 mmol) of the compound from Example 122A in 30 ml of ethanol and 7 ml of ethyl acetate under argon, and the mixture was stirred at 40° C. for 1 h. The reaction mixture was added to saturated aqueous ammonium chloride solution and ethyl acetate, the phases were separated, the aqueous phase was extracted twice with ethyl acetate, and the combined organic phases were dried over magnesium sulfate, filtered and concentrated. The crude product was purified by flash chromatography on silica gel (mobile phase: toluene/ethyl acetate gradient) to result in 1.64 g (95% of theory) of a mixture of the diastereomers of the title compound.

후처리

  1. customthe phases were separated
  2. extractionthe aqueous phase was extracted twice with ethyl acetate
  3. dry with materialthe combined organic phases were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by flash chromatography on silica gel (mobile phase: toluene/ethyl acetate gradient)

출처 및 근거

ORD 기록
ord-324117239c8f4f05bd089775e9e08d38
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08063234B2

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