Sodium Hydroxide → N-t-butyl-3,3-diphenylcyclopentylamine

HRID 1657265Notes

Reaction equation

HRID 1657265 reaction equation
CS(O)(=O)=O.[C:6]([NH:10][CH:11]1[CH2:15][C:14]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:13]=[CH:12]1)([CH3:9])([CH3:8])[CH3:7].[OH-].[Na+]>C(OCC)(=O)C>[C:6]([NH:10][CH:11]1[CH2:12][CH2:13][C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:15]1)([CH3:9])([CH3:7])[CH3:8]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 19787492(-)-N-t-butyl-4,4-diphenyl-2-cyclopentenylamine methanesulfonate

Product 1

HCID 10379659N-t-butyl-3,3-diphenylcyclopentylamineYield 100%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of (-)-N-t-butyl-4,4-diphenyl-2-cyclopentenylamine methanesulfonate (0.70 g) in ethyl acetate was added 2N sodium hydroxide aqueous solution (10 ml), and the organic layer was separated. The solution was washed with brine and hydrogenated over 10% palladium-on-carbon (0.06 g) to give (-)-N-t-butyl-3,3-diphenylcyclopentylamine (0.53 g). To a solution of (-)-N-t-butyl-3,3-diphenylcyclopentylamine (0.53 g) in chloroform was added a solution of methanesulfonic acid (174 mg) in methanol. The solvent was evaporated in vacuo and triturated with diethyl ether to give (-)-N-t-butyl-3,3-diphenylcyclopentylamine methanesulfonate (0.63 g).

Workup

  1. customthe organic layer was separated
  2. washThe solution was washed with brine

Sources & evidence

ORD record
ord-687d97abcb4f420285a163c83248eedd
Source dataset
uspto-grants-1993_10
Patent number
US05256824

Reaction notes

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