1,1-Dimethylethyl (3R)-3-[[(phenylmethoxy)carbonyl]amino]-1-pyrrolidinecarboxylate → (R)-(+)-1-Boc-3-aminopyrrolidine

HRID 2079412Notes

Reaction equation

HRID 2079412 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@@H:10]([NH:13]C(=O)OCC2C=CC=CC=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[NH2:13][C@@H:10]1[CH2:11][CH2:12][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:9]1

Participants

4

Reactant 1

HCID 115370521,1-Dimethylethyl (3R)-3-[[(phenylmethoxy)carbonyl]amino]-1-pyrrolidinecarboxylate

Product 1

HCID 854070(R)-(+)-1-Boc-3-aminopyrrolidine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Under an N2 atmosphere, a solution of benzyl (R)-1-(tert-butoxycarbonyl)pyrrolidin-3-ylcarbamate (1.85 g, 5.75 mmol) in 10 mL MeOH was added to a flask containing Pd/C (185 mg, 10% weight Pd on carbon). After evacuating the flask under vacuum and purging it twice with N2, the reaction was stirred for 3 h under an H2 atmosphere at ambient pressure. The reaction was filtered through a bed of Celite, and the solvent was evaporated under reduced pressure to obtain (R)-tert-butyl 3-aminopyrrolidine-1-carboxylate which was used without further purification. LC/MS: m/z 187.3 (M+H)+ at 1.07 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Workup

  1. customAfter evacuating the flask under vacuum
  2. custompurging it twice with N2
  3. filtrationThe reaction was filtered through a bed of Celite
  4. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-c5fa2ae183f54aa0b67c320b14030d13
Source dataset
uspto-grants-2011_04
Patent number
US07928107B2

Reaction notes

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