Sodium borohydride → 1-[(2'-t-Butoxycarbonylbiphenyl-4-yl)methyl]2-butyl-4-(1-hydroxypropyl)imidazole-5-carbonitrile

HRID 52923Notes

Reaction equation

HRID 52923 reaction equation
[C:1]([O:5][C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]1[CH:19]=[CH:18][C:17]([CH2:20][N:21]2[C:25]([C:26]#[N:27])=[C:24]([C:28](=[O:31])[CH2:29][CH3:30])[N:23]=[C:22]2[CH2:32][CH2:33][CH2:34][CH3:35])=[CH:16][CH:15]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>C(O)C>[C:1]([O:5][C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]1[CH:19]=[CH:18][C:17]([CH2:20][N:21]2[C:25]([C:26]#[N:27])=[C:24]([CH:28]([OH:31])[CH2:29][CH3:30])[N:23]=[C:22]2[CH2:32][CH2:33][CH2:34][CH3:35])=[CH:16][CH:15]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 190361561-[(2'-t-Butoxycarbonylbiphenyl-4-yl)methyl]-2-butyl-4-propionylimidazole-5-carbonitrile

Product 1

HCID 190362781-[(2'-t-Butoxycarbonylbiphenyl-4-yl)methyl]2-butyl-4-(1-hydroxypropyl)imidazole-5-carbonitrileYield 81.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Following a procedure similar to that described in Example 45(b), but using 451 mg of 1-[(2'-t-butoxycarbonylbiphenyl-4-yl)methyl]-2-butyl-4-propionylimidazole-5-carbonitrile [prepared as described in step (a) above] and 36 mg of sodium borohydride in 10 ml of ethanol, 369 mg of the title compound were obtained as a viscous oil.

Sources & evidence

ORD record
ord-bae0b5e3a19649d4983be84bd4025dcc
Source dataset
uspto-grants-1997_04
Patent number
US05616599

Reaction notes

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