Ammonium Chloride → 2-[(2,4-Difluorophenyl)(hydroxy)methyl]cyclopropanecarbonitrile

HRID 561486Notes

Reaction equation

HRID 561486 reaction equation
[BH4-].[Na+].[F:3][C:4]1[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:5]=1[C:6]([CH:8]1[CH2:10][CH:9]1[C:11]#[N:12])=[O:7].[Cl-].[NH4+]>C(O)C.C(OCC)(=O)C>[F:3][C:4]1[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:5]=1[CH:6]([OH:7])[CH:8]1[CH2:10][CH:9]1[C:11]#[N:12]

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 583925512-(2,4-Difluorobenzoyl)cyclopropanecarbonitrile

Product 1

HCID 583924722-[(2,4-Difluorophenyl)(hydroxy)methyl]cyclopropanecarbonitrile

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
40 °C

Procedure

342 mg (9.03 mmol) of sodium borohydride were added to 1.70 g (8.21 mmol) of the compound from Example 123A in 35 ml of ethanol and 15 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 9/1) to result in 1.50 g (87% of theory) of a mixture of the diastereomers of the title compound.

Workup

  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 9/1)

Sources & evidence

ORD record
ord-80b5b8dcd3ad4307a8e5f123e6e73631
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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