Trifluoroacetic acid → (S)-(-)-3-benzoyloxypyrrolidine

HRID 270104Notes

Reaction equation

HRID 270104 reaction equation
[C:1]([O:9][C@H:10]1[CH2:14][CH2:13][N:12](C(OC(C)(C)C)=O)[CH2:11]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(C(O)=O)(F)(F)F>C(Cl)Cl>[NH:12]1[CH2:13][CH2:14][C@H:10]([O:9][C:1](=[O:8])[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:11]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 15117240(S)-3-benzoyloxy-1-t-butoxycarbonylpyrrolidine

Product 1

HCID 11160511(S)-(-)-3-benzoyloxypyrrolidineYield 191.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl(3S)-3-(benzoyloxy)pyrrolidine-1-carboxylate (635 mg, 2.18 mmol) was treated with 20% CF3CO2H in CH2Cl2 (20 mL) overnight at room temperature. The volatiles were removed in vacuo to give the subtitled compound (800 mg).

Workup

  1. customThe volatiles were removed in vacuo

Sources & evidence

ORD record
ord-96299a21fef14d52987af93699393fb9
Source dataset
uspto-grants-2008_11
Patent number
US07449475B2

Reaction notes

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