Methanesulfonic Acid → N-t-butyl-3,3-diphenylcyclopentylamine methanesulfonate

HRID 1657266Notes

Reaction equation

HRID 1657266 reaction equation
[C:1]([NH:5][CH:6]1[CH2:10][CH2:9][C:8]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:7]1)([CH3:4])([CH3:3])[CH3:2].[CH3:23][S:24]([OH:27])(=[O:26])=[O:25]>C(Cl)(Cl)Cl.CO>[CH3:23][S:24]([OH:27])(=[O:26])=[O:25].[C:1]([NH:5][CH:6]1[CH2:10][CH2:9][C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH2:7]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 6395Methanesulfonic AcidHCID 10379659N-t-butyl-3,3-diphenylcyclopentylamine

Product 1

HCID 19787464N-t-butyl-3,3-diphenylcyclopentylamine methanesulfonateYield 89.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

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 solvent was evaporated in vacuo
  2. customtriturated with diethyl ether

Sources & evidence

ORD record
ord-1634c3adb6ae45d4b58360617a045582
Source dataset
uspto-grants-1993_10
Patent number
US05256824

Reaction notes

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