Sodium borohydride → 2-(4-Chlorophenyl)cyclobutanamine

HRID 1482439Notes

Reaction equation

HRID 1482439 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:11][CH2:10][C:9]2=[N:12]O)=[CH:4][CH:3]=1.[BH4-].[Na+]>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[CH2:11][CH2:10][CH:9]2[NH2:12])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 1317367062-(4-Chlorophenyl)cyclobutanone oxime

Product 1

HCID 810131342-(4-Chlorophenyl)cyclobutanamineYield 66.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-(4-chlorophenyl)cyclobutanone oxime (200 mg, 1 mmol) in methanol (5 ml) was added MoO3 (205 mg, 1.4 eq.) and sodium borohydride (394 mg, 10 eq) at 0° C. After stirring at rt for 2 h the solvent was evaporated. A mixture of H2O and CH2Cl2 was added. Organic phase was separated, washed with brine, dried and concentrated in vacuo. 120 mg of product-amine was isolated as a mixture of cis and trans isomers 2:1. The crude product without purification was used for the next reaction.

Workup

  1. customwas evaporated
  2. additionA mixture of H2O and CH2Cl2
  3. additionwas added
  4. customOrganic phase was separated
  5. washwashed with brine
  6. customdried
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f804baaaeea3454cb98a328cec5f7536
Source dataset
uspto-grants-2016_08
Patent number
US09414589B2

Reaction notes

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