Sodium borohydride → tert-Butyl 4-[2-(hydroxymethyl)phenyl]piperazine-1-carboxylate

HRID 974877Notes

Reaction equation

HRID 974877 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[CH:20]=[O:21])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>CO>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[CH2:20][OH:21])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 64909901-Boc-4-(2-formylphenyl)piperazine

Product 1

HCID 7127802tert-Butyl 4-[2-(hydroxymethyl)phenyl]piperazine-1-carboxylateYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1.15 g (3.96 mmol) of 1-t-butoxycarbonyl-4-(2-formyl-phenyl)-piperazine in 10 mL of MeOH was treated with 0.15 g (3.96 mmol) of NaBH4. After 2 h the reaction was quenched by adding 1.2N HCl and the mixture was extracted with EtOAc. The EtOAc solution was washed with water, brine and dried. The filtrate was concentrated to yield 1.1 g (95%) of 1-t-butoxycarbonyl-4-(2-hydroxymethyl-phenyl)-piperazine as a white foam which was used without purification.

Workup

  1. customAfter 2 h the reaction was quenched
  2. additionby adding 1.2N HCl
  3. extractionthe mixture was extracted with EtOAc
  4. washThe EtOAc solution was washed with water, brine
  5. customdried
  6. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-91444b4b707f4d42a65db25e5792c841
Source dataset
uspto-grants-1997_03
Patent number
US05607936

Reaction notes

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