Ammonium Chloride → 2-{Hydroxy[4-(trifluoromethyl)phenyl]methyl}cyclopropanecarbonitrile
Reaction equation
[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]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 40 °C
Procedure
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.
Workup
- customthe phases were separated
- extractionthe aqueous phase was extracted twice with ethyl acetate
- dry with materialthe combined organic phases were dried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated
- customThe crude product was purified by flash chromatography on silica gel (mobile phase: toluene/ethyl acetate gradient)
Sources & evidence
- ORD record
- ord-324117239c8f4f05bd089775e9e08d38
- Source dataset
- uspto-grants-2011_11
- Patent number
- US08063234B2
Reaction notes
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