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

HRID 561484ノート

反応式

HRID 561484 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 8857Ethyl Acetate溶媒2 回

反応条件

温度
40 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-324117239c8f4f05bd089775e9e08d38
出典データセット
uspto-grants-2011_11
特許番号
US08063234B2

反応ノート

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