tert-Butyl ((1-benzylpyrrolidin-3-yl)methyl)carbamate → tert-butyl N-((pyrrolidin-3-yl)methyl)carbamate

HRID 1276361Notes

Reaction equation

HRID 1276361 reaction equation
C([N:8]1[CH2:12][CH2:11][CH:10]([CH2:13][NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:9]1)C1C=CC=CC=1>CO.C(O)(=O)C.[Pd]>[C:18]([O:17][C:15]([NH:14][CH2:13][CH:10]1[CH2:11][CH2:12][NH:8][CH2:9]1)=[O:16])([CH3:21])([CH3:19])[CH3:20]

Participants

5

Reactant 1

HCID 5108694tert-Butyl ((1-benzylpyrrolidin-3-yl)methyl)carbamate

Product 1

HCID 4250767tert-butyl N-((pyrrolidin-3-yl)methyl)carbamate

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent2×HCID 887MethanolSolvent2×

Procedure

1-Benzyl-3-(RS)-(N-tert-butoxycarbonylaminomethyl)pyrrolidine (22.2 g, 0.76 mol) was dissolved in a mixture of methanol and acetic acid (1:1, 100 mL) and added to a Parr flask charged with palladium on carbon (10%, 4 g) suspended in methanol and acetic acid (1:1, 100 mL). The flask was transferred to the Parr reduction apparatus and the suspension shaken under an atmosphere of hydrogen at 60 psi for 2 days. The reaction mixture was filtered through a celite plug, eluting with a mixture of methanol/methylene chloride. The solvent was concentrated and the residue co-evaporated with toluene to afford 3-(RS)-(N-tert-butoxycarbonylaminomethyl)pyrrolidine as a colorless oil which was used directly.

Workup

  1. additionadded to a Parr flask
  2. filtrationThe reaction mixture was filtered through a celite plug
  3. washeluting with a mixture of methanol/methylene chloride
  4. concentrationThe solvent was concentrated

Sources & evidence

ORD record
ord-738e6932d1904d3aab0908b8f2bcecb6
Source dataset
uspto-grants-2000_12
Patent number
US06166015

Reaction notes

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