Methanesulfonic Acid → (-)-N-t-butyl-4,4-diphenyl-2-cyclopentenylamine methanesulfonate

HRID 1657264Notes

Reaction equation

HRID 1657264 reaction equation
[C:1]([NH:5][CH:6]1[CH2:10][C:9]([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)[CH:8]=[CH:7]1)([CH3:4])([CH3:3])[CH3:2].[CH3:23][S:24]([OH:27])(=[O:26])=[O:25]>C(OCC)(=O)C>[CH3:23][S:24]([OH:27])(=[O:26])=[O:25].[C:1]([NH:5][CH:6]1[CH2:10][C:9]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:8]=[CH:7]1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 9796063N-t-butyl-4,4-diphenyl-2-cyclopentenylamine

Product 1

HCID 19787492(-)-N-t-butyl-4,4-diphenyl-2-cyclopentenylamine methanesulfonateYield 83.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of (-)-N-t-butyl-4,4-diphenyl-2-cyclopentenylamine (3.54 g) in ethyl acetate (20 ml) was added a solution of methanesulfonic acid (1.16 g) in ethyl acetate (1 ml). The solvent was evaporated in vacuo and diethyl ether was added. After kept standing for 4 hours, the resulting precipitate was collected by filtration to give (-)-N-t-butyl-4,4-diphenyl-2-cyclopentenylamine methanesulfonate (3.90 g).

Workup

  1. customThe solvent was evaporated in vacuo and diethyl ether
  2. additionwas added
  3. filtrationthe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-f46364230c184237bb9b6d5ef62927f2
Source dataset
uspto-grants-1993_10
Patent number
US05256824

Reaction notes

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