Sodium borohydride → HCID 21193240, compound

HRID 443293Notes

Reaction equation

HRID 443293 reaction equation
[C:1]([C:3]1[CH:30]=[CH:29][C:6]([CH2:7][N:8]2[C:12]([CH2:13][N:14]3[CH2:19][CH2:18][CH:17]([C:20](=[O:28])[C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([CH3:27])[CH:22]=4)[CH2:16][CH2:15]3)=[CH:11][N:10]=[CH:9]2)=[CH:5][CH:4]=1)#[N:2].[BH4-].[Na+]>CO>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]2[C:12]([CH2:13][N:14]3[CH2:15][CH2:16][CH:17]([CH:20]([OH:28])[C:21]4[CH:22]=[C:23]([CH3:27])[CH:24]=[CH:25][CH:26]=4)[CH2:18][CH2:19]3)=[CH:11][N:10]=[CH:9]2)=[CH:29][CH:30]=1)#[N:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 21193363HCID 21193363, compound

Product 1

HCID 21193240HCID 21193240, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1-[3-(4-cyanobenzyl)-3H-imidazol-4-ylmethyl]-4-(3-methylbenzoyl)piperidine (175 mg, 0.44 mmol; Example 104) in methanol (5 mL) was treated with sodium borohydride (12 mg, 0.31 mmol) at room temp. The resultant solution was stirred at room temp. for 30 min., and concentrated under vacuum. The residue was subjected to column chromatography on silica gel eluting with chloroform saturated with ammonia gas. Collection and concentration of appropriate fractions provided the title product.

Workup

  1. concentrationconcentrated under vacuum
  2. customCollection and concentration of appropriate fractions

Sources & evidence

ORD record
ord-566ebfcc28d249c38c60b90454905973
Source dataset
uspto-grants-1999_04
Patent number
US05891889

Reaction notes

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