4-tert-Butylcyclohexanone → HCID 14406817, compound

HRID 974180Notes

Reaction equation

HRID 974180 reaction equation
[C:1]([CH:5]1[CH2:10][CH2:9][C:8](=O)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].[C:12]([C:16]1[CH:21]=[CH:20][C:19]([CH:22]2[CH2:26][CH2:25][NH:24][CH2:23]2)=[CH:18][CH:17]=1)([CH3:15])([CH3:14])[CH3:13].C([BH3-])#N.[Na+]>CO.[Cl-].[Zn+2].[Cl-]>[C:1]([CH:5]1[CH2:10][CH2:9][CH:8]([N:24]2[CH2:25][CH2:26][CH:22]([C:19]3[CH:20]=[CH:21][C:16]([C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:17][CH:18]=3)[CH2:23]2)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 73924-tert-ButylcyclohexanoneHCID 5003444Sodium cyanoborohydrideHCID 144068163-[4-(1,1-Dimethylethyl)phenyl]pyrrolidine

Product 1

HCID 14406817HCID 14406817, compound

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 887MethanolSolvent

Procedure

15.4 g (100 millimoles) of 4-tert-butylcyclohexanone, 9.8 g (48 millimoles) of 3-(4-tert-butylphenyl)-pyrrolidine, 6.8 g (50 millimoles) of zinc(II) chloride and 6.3 g (100 millimoles) of sodium cyanoborohydride in 200 ml of absolute methanol were stirred for 48 hours at 22° C. The methanol was distilled off under reduced pressure and the residue was dissolved in dichloromethane and 5% strength sodium hydroxide solution.

Workup

  1. distillationThe methanol was distilled off under reduced pressure
  2. dissolutionthe residue was dissolved in dichloromethane

Sources & evidence

ORD record
ord-b6c1614e8ca847e8ba6d23843b2b98c1
Source dataset
uspto-grants-1991_11
Patent number
US05068245

Reaction notes

Loading…