Water → HCID 22161771, compound

HRID 1088796Notes

Reaction equation

HRID 1088796 reaction equation
[O:1]=[C:2]1[C:11]2[C:6](=[C:7]([CH2:12][O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])[CH:8]=[CH:9][CH:10]=2)[N:5]([CH2:21][CH3:22])[CH2:4][CH2:3]1.[BH4-].[Na+].O>CO>[Si:14]([O:13][CH2:12][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:6]=1[N:5]([CH2:21][CH3:22])[CH2:4][CH2:3][CH:2]2[OH:1])([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15]

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 22161781HCID 22161781, compound

Product 1

HCID 22161771HCID 22161771, compoundYield 105.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-oxo-8-t-butyldimethylsilyloxymethyl-1-ethyl-1,2,3,4-tetrahydroquinoline (2.17 g) was dissolved in methanol (20 ml). To this solution was added sodium borohydride (0.26 g) at room temperature, and the mixture was stirred for 10 minutes. Water was added to the reaction mixture and the solvent was distilled off to give 8-t-butyldimethylsilyloxymethyl-4-hydroxy-1-ethyl-1,2,3,4-tetrahydroquinoline (2.30 g).

Workup

  1. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-fbc7ccb2f1fe40f380580a8d07266d3d
Source dataset
uspto-grants-1990_10
Patent number
US04963566

Reaction notes

Loading…