(R)-Benzyl 3-((tert-butoxycarbonyl)(methyl)amino)pyrrolidine-1-carboxylate → tert-Butyl methyl((3R)-pyrrolidin-3-yl)carbamate

HRID 1825108Notes

Reaction equation

HRID 1825108 reaction equation
[C:1]([O:5][C:6]([N:8]([CH3:24])[C@@H:9]1[CH2:13][CH2:12][N:11](C(OCC2C=CC=CC=2)=O)[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[OH-].[OH-].[Pd+2]>[CH3:24][N:8]([C@@H:9]1[CH2:13][CH2:12][NH:11][CH2:10]1)[C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 58940619(R)-Benzyl 3-((tert-butoxycarbonyl)(methyl)amino)pyrrolidine-1-carboxylate

Product 1

HCID 7019173tert-Butyl methyl((3R)-pyrrolidin-3-yl)carbamate

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a stirred solution of benzyl (3R)-3-[(tert-butoxycarbonyl)(methyl)amino]pyrrolidine-1-carboxylate 34a (1.5 g, 5.17 mmole) in MeOH (10 ml) was added Pd(OH)2 on carbon (150 mg). The reaction mixture was under 1 atmosphere of H2 overnight, filtered through celite and concentrated, in vacuo. The residue obtained was used directly in the subsequent reaction without any further purification, vide infra. 1H NMR (300 MHz, CD3OD) δ 4.47 (1H, m), 3.20 (1H, m), 2.91 (2H, m), 2.76 (1H, m), 2.69 (3H, s), 1.89 (1H, m), 1.68 (1H, m), 1.35 (9H, s).

Workup

  1. customwas under 1 atmosphere of H2 overnight
  2. filtrationfiltered through celite and
  3. concentrationconcentrated, in vacuo
  4. customThe residue obtained
  5. customwas used directly in the subsequent reaction without any further purification, vide infra

Sources & evidence

ORD record
ord-312becc83058448da66cc5bd2cd9b9a2
Source dataset
uspto-grants-2006_05
Patent number
US07045528B2

Reaction notes

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