4-tert-Butylcyclohexanone → HCID 14406791, compound

HRID 974181Notes

Reaction equation

HRID 974181 reaction equation
[CH3:1][CH:2]1[CH:6]([C:7]2[CH:12]=[CH:11][C:10]([C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:9][CH:8]=2)[CH2:5][NH:4][CH2:3]1.[C:17]([CH:21]1[CH2:26][CH2:25][C:24](=O)[CH2:23][CH2:22]1)([CH3:20])([CH3:19])[CH3:18].C([BH3-])#N.[Na+]>CO.[Cl-].[Zn+2].[Cl-]>[C:17]([CH:21]1[CH2:26][CH2:25][CH:24]([N:4]2[CH2:5][CH:6]([C:7]3[CH:8]=[CH:9][C:10]([C:13]([CH3:15])([CH3:14])[CH3:16])=[CH:11][CH:12]=3)[CH:2]([CH3:1])[CH2:3]2)[CH2:23][CH2:22]1)([CH3:20])([CH3:19])[CH3:18]

Participants

6

Reactant 3

HCID 73924-tert-ButylcyclohexanoneHCID 5003444Sodium cyanoborohydrideHCID 14406790HCID 14406790, compound

Product 1

HCID 14406791HCID 14406791, compound

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 887MethanolSolvent

Procedure

2.17 g (10 millimoles) of 3-methyl-4-(4-tert-butylphenyl)-pyrrolidine (80% of transisomer), 1.54 g (10 millimoles) of 4-tert-butylcyclohexanone, 0.75 g (5.5 millimoles) of zinc(II) chloride and 0.70 g (11 millimoles) of sodium cyanoborohydride in 100 ml of absolute methanol are stirred for 48 hours at 20° C. The solvent is evaporated under reduced pressure, and the residue is dissolved in 5% strength sodium hydroxide solution and methyl tert-butyl ether. The organic phase is washed with sodium chloride solution and water, dried and evaporated under reduced pressure, and the residue is subjected to incipient distillation under 0.4 bar at up to 140° C. Yield: 1.9 g (54%) of a viscous resin.

Workup

  1. customThe solvent is evaporated under reduced pressure
  2. dissolutionthe residue is dissolved in 5% strength sodium hydroxide solution and methyl tert-butyl ether
  3. washThe organic phase is washed with sodium chloride solution and water
  4. customdried
  5. customevaporated under reduced pressure
  6. distillationthe residue is subjected to incipient distillation under 0.4 bar at up to 140° C

Sources & evidence

ORD record
ord-201cae9272c34a619e041a06a066f8c9
Source dataset
uspto-grants-1991_11
Patent number
US05068246

Reaction notes

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