p-Toluenesulfonic acid monohydrate → (3R)-3-Methoxypyrrolidine 4-methylbenzenesulfonate

HRID 1445780Notes

Reaction equation

HRID 1445780 reaction equation
O.[C:2]1([CH3:12])[CH:7]=[CH:6][C:5]([S:8]([OH:11])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH3:13][O:14][C@@H:15]1[CH2:19][CH2:18][N:17](C(OC(C)(C)C)=O)[CH2:16]1.CO[C@@H]1CCNC1>C(O)C>[CH3:12][C:2]1[CH:3]=[CH:4][C:5]([S:8]([OH:11])(=[O:10])=[O:9])=[CH:6][CH:7]=1.[CH3:13][O:14][C@@H:15]1[CH2:19][CH2:18][NH:17][CH2:16]1

Participants

5

Reactant 3

HCID 521998p-Toluenesulfonic acid monohydrateHCID 15086791(R)-3-Methoxypyrrolidine2×HCID 34179484(R)-tert-Butyl 3-methoxypyrrolidine-1-carboxylate

Product 1

HCID 86614639(3R)-3-Methoxypyrrolidine 4-methylbenzenesulfonate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Prepare using the method of Intermediate 49 with p-toluenesulfonic acid monohydrate (0.207 g, 1.09 mmol), crude tert-butyl (3R)-3-methoxypyrrolidine-1-carboxylate and (3R)-3-methoxypyrrolidine (See Intermediate 58) (0.42 g, 1.09 mmol) and ethanol (2 mL) to give the title compound as a red solid (0.42 g): MS (m/e): 102(M+1).

Workup

  1. customPrepare

Sources & evidence

ORD record
ord-33e9673998eb4534a32c95679252fa75
Source dataset
uspto-grants-2010_02
Patent number
US07666871B2

Reaction notes

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