Hexane → tert-butyl (3S,4R)-3-amino-4-(3,4-dichlorophenyl)pyrrolidine-1-carboxylate p-toluenesulfonate

HRID 1260942Notes

Reaction equation

HRID 1260942 reaction equation
[NH2:1][C@H:2]1[C@H:6]([C:7]2[CH:12]=[CH:11][C:10]([Cl:13])=[C:9]([Cl:14])[CH:8]=2)[CH2:5][N:4]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:3]1.O.[C:23]1([CH3:33])[CH:28]=[CH:27][C:26]([S:29]([OH:32])(=[O:31])=[O:30])=[CH:25][CH:24]=1.CCCCCC>C(OCC)(=O)C>[C:23]1([CH3:33])[CH:24]=[CH:25][C:26]([S:29]([OH:32])(=[O:30])=[O:31])=[CH:27][CH:28]=1.[NH2:1][C@H:2]1[C@H:6]([C:7]2[CH:12]=[CH:11][C:10]([Cl:13])=[C:9]([Cl:14])[CH:8]=2)[CH2:5][N:4]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:3]1

Participants

5

Reactant 3

HCID 8058HexaneHCID 521998p-Toluenesulfonic acid monohydrateHCID 58356102tert-butyl (3S,4R)-3-amino-4-(3,4-dichlorophenyl)pyrrolidine-1-carboxylate

Product 1

HCID 86631350tert-butyl (3S,4R)-3-amino-4-(3,4-dichlorophenyl)pyrrolidine-1-carboxylate p-toluenesulfonateYield 88.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the compound (0.92 g) obtained in step 5 in ethyl acetate (8 mL) was added p-toluenesulfonic acid monohydrate (0.53 g), and then hexane (1.5 mL) was added. The precipitate was collected by filtration to give tert-butyl (3S,4R)-3-amino-4-(3,4-dichlorophenyl)pyrrolidine-1-carboxylate p-toluenesulfonate (1.24 g, 77%).

Workup

  1. filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record
ord-114adbfe6b7b4c63bc70e43d24693b8f
Source dataset
uspto-grants-2013_06
Patent number
US08470816B2

Reaction notes

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