Sodium borohydride → 1-[(1,2,3,4-Tetrahydro-1-hydroxy-2-naphthalenyl)methyl]-4-anilino isonipecotamide

HRID 2072480Notes

Reaction equation

HRID 2072480 reaction equation
Cl.[O:2]=[C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][CH2:5][CH:4]1[CH2:13][N:14]1[CH2:22][CH2:21][C:17]([NH:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)([C:18]([NH2:20])=[O:19])[CH2:16][CH2:15]1.[BH4-].[Na+]>CO.O>[OH:2][CH:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][CH2:5][CH:4]1[CH2:13][N:14]1[CH2:15][CH2:16][C:17]([NH:23][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)([C:18]([NH2:20])=[O:19])[CH2:21][CH2:22]1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 1317109071-[(1,2,3,4-Tetrahydro-1-oxo-2-naphthalenyl)-methyl]-4-anilino isonipecotamide, hydrochloride

Product 1

HCID 214082471-[(1,2,3,4-Tetrahydro-1-hydroxy-2-naphthalenyl)methyl]-4-anilino isonipecotamide

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Finely-ground 1-[(1,2,3,4-tetrahydro-1-oxo-2-naphthalenyl)-methyl]-4-anilino isonipecotamide, hydrochloride (1:1) (5.0 g) is slurried in methanol (100 ml) and cooled in ice. To this mixture is added an aqueous solution of sodium borohydride (3.0 g) in water (25 ml). The resulting mixture is stirred for 15 hours at room temperature under nitrogen. Dilution of the reaction mixture with water (200 ml), extraction with methylene chloride, and concentration of the dried organic solution give the title compound.

Workup

  1. temperaturecooled in ice
  2. extractionDilution of the reaction mixture with water (200 ml), extraction with methylene chloride, and concentration of the dried organic solution

Sources & evidence

ORD record
ord-bbdaaa48d645472e9f685043da524c8f
Source dataset
uspto-grants-1977_09
Patent number
US04051248

Reaction notes

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