Trifluoroacetic acid → benzyl ((R)-pyrrolidin-3-yl)methylcarbamate

HRID 639063Notes

Reaction equation

HRID 639063 reaction equation
[C:1]1([CH2:7][O:8][C:9]([NH:11][CH2:12][C@@H:13]2[CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14]2)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[C:1]1([CH2:7][O:8][C:9](=[O:10])[NH:11][CH2:12][C@@H:13]2[CH2:17][CH2:16][NH:15][CH2:14]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59254364(S)-tert-Butyl 3-((((benzyloxy)carbonyl)amino)methyl)pyrrolidine-1-carboxylate

Product 1

HCID 45072660benzyl ((R)-pyrrolidin-3-yl)methylcarbamateYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1,1-dimethylethyl(3S)-3-[({[(phenylmethyl)oxy]carbonyl}amino)methyl]-1-pyrrolidinecarboxylate in DCM (100 mL) at RT was added TFA (50 mL). After 2 h, the reaction solution was concentrated under vacuum and purified on silica (CHCl3/MeOH, 9:1 containing 5% NH4OH) to give the title compound (2.93 g, 94%) as a light yellow oil: LC-MS (ES) m/e 235 (M+H)+.

Workup

  1. concentrationthe reaction solution was concentrated under vacuum
  2. custompurified on silica (CHCl3/MeOH, 9:1 containing 5% NH4OH)

Sources & evidence

ORD record
ord-90eda06919574eed86fa7e50d5deeb70
Source dataset
uspto-grants-2010_04
Patent number
US07691850B2

Reaction notes

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