Sodium borohydride → 5-benzyloxy-2-[3-(4-cyanophenoxy)-2-hydroxy-3-methylbutyl]pyridine N-oxide

HRID 1073941Notes

Reaction equation

HRID 1073941 reaction equation
[BH4-].[Na+].[CH2:3]([O:10][C:11]1[CH:12]=[CH:13][C:14]([CH2:18][C:19](=[O:32])[C:20]([O:23][C:24]2[CH:29]=[CH:28][C:27]([C:30]#[N:31])=[CH:26][CH:25]=2)([CH3:22])[CH3:21])=[N+:15]([O-:17])[CH:16]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>C(O)C.O>[CH2:3]([O:10][C:11]1[CH:12]=[CH:13][C:14]([CH2:18][CH:19]([OH:32])[C:20]([O:23][C:24]2[CH:29]=[CH:28][C:27]([C:30]#[N:31])=[CH:26][CH:25]=2)([CH3:22])[CH3:21])=[N+:15]([O-:17])[CH:16]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 543932385-benzyloxy-2-[3-(4-cyanophenoxy)-3-methyl-2-oxobutyl]pyridine N-oxide

Product 1

HCID 545624775-benzyloxy-2-[3-(4-cyanophenoxy)-2-hydroxy-3-methylbutyl]pyridine N-oxideYield 80.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

0.46 g of sodium borohydride was added to a stirred solution of 4.53 g of 5-benzyloxy-2-[3-(4-cyanophenoxy)-3-methyl-2-oxobutyl]pyridine N-oxide in 60 ml of ethanol. After 2 hours the solution was diluted with 200 ml of water and extracted with diethyl ether. The organic phase was evaporated to give 3.67 g of 5-benzyloxy-2-[3-(4-cyanophenoxy)-2-hydroxy-3-methylbutyl]pyridine N-oxide of melting point 125° C. after recrystallization from ethanol

Workup

  1. extractionextracted with diethyl ether
  2. customThe organic phase was evaporated

Sources & evidence

ORD record
ord-8d064181189e42819b3746425ca7ca70
Source dataset
uspto-grants-1990_11
Patent number
US04971982

Reaction notes

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