Trifluoroacetic acid → 3-(4-Nitrophenoxy)pyrrolidine

HRID 515266Notes

Reaction equation

HRID 515266 reaction equation
[N+:1]([C:4]1[CH:22]=[CH:21][C:7]([O:8][CH:9]2[CH2:13][CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].FC(F)(F)C(O)=O>ClCCl>[N+:1]([C:4]1[CH:22]=[CH:21][C:7]([O:8][CH:9]2[CH2:13][CH2:12][NH:11][CH2:10]2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 21918683tert-Butyl 3-(4-nitrophenoxy)pyrrolidine-1-carboxylate

Product 1

HCID 219186903-(4-Nitrophenoxy)pyrrolidineYield 104.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 3-(4-nitrophenoxy)pyrrolidine-1-carboxylate (9.73 mmol, 3 g) was dissolved in dichloromethane (2.5 mL). Trifluoroacetic acid (1 mL) was added and the reaction mixture stirred at room temperature for 30 minutes. The reaction was purified by SCX chromatography to give the title compound (2.11 g). MS (ESI) m/z 209.0 [M+H]+

Workup

  1. customThe reaction was purified by SCX chromatography

Sources & evidence

ORD record
ord-54bb31743a8643388a9fed0be0dfd105
Source dataset
uspto-grants-2015_08
Patent number
US09108939B2

Reaction notes

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