Ammonium Chloride → 2-[(4-Chloro-2-methoxyphenyl)(hydroxy)methyl]cyclopropanecarbonitrile

HRID 561487Notes

Reaction equation

HRID 561487 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[CH:16]=[CH:15][C:7]([C:8]([CH:10]2[CH2:12][CH:11]2[C:13]#[N:14])=[O:9])=[C:6]([O:17][CH3:18])[CH:5]=1.[Cl-].[NH4+]>C(O)C.C(OCC)(=O)C>[Cl:3][C:4]1[CH:16]=[CH:15][C:7]([CH:8]([OH:9])[CH:10]2[CH2:12][CH:11]2[C:13]#[N:14])=[C:6]([O:17][CH3:18])[CH:5]=1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 583925482-(4-Chloro-2-methoxybenzoyl)cyclopropanecarbonitrile

Product 1

HCID 583921672-[(4-Chloro-2-methoxyphenyl)(hydroxy)methyl]cyclopropanecarbonitrile

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
40 °C

Procedure

49.1 mg (1.30 mmol) of sodium borohydride were added to 278 mg (1.18 mmol) of the compound from Example 128A in 23 ml of ethanol and 10 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. 190 mg (68% of theory) of a mixture of the diastereomerse of the title compound were obtained.

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. addition190 mg (68% of theory) of a mixture of the diastereomerse of the title compound
  7. customwere obtained

Sources & evidence

ORD record
ord-ba2998ad433c40a19f09f0b1407492c4
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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