1-Benzyl-3-(tert-butoxycarbonylamino)pyrrolidine → tert-butyl N-(pyrrolidin-3-yl)carbamate

HRID 465000Notes

Reaction equation

HRID 465000 reaction equation
C1(C[N:8]2[CH2:12][CH2:11][CH:10]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:9]2)C=CC=CC=1.[H][H]>[Pd].O1CCCC1>[NH:8]1[CH2:12][CH2:11][CH:10]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:18])([CH3:17])[CH3:19])[CH2:9]1

Participants

5

Reactant 2

HCID 35758231-Benzyl-3-(tert-butoxycarbonylamino)pyrrolidineHCID 178418361HCID 178418361, compound

Product 1

HCID 2757234tert-butyl N-(pyrrolidin-3-yl)carbamateYield 9.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 101.5 g (0.37 mole) of 1,1-dimethylethyl [1-(phenylmethyl)-3-pyrrolidinyl]carbamate, 5.0 g of 20% Palladium on carbon and 1 liter of tetrahydrofuran was shaken in an atmosphere of hydrogen at about 50 psi and room temperature for 24 hours. The catalyst was removed by filtering through Celite, and the filtrate was concentrated in vacuo to give 6.8 g of 1,1-dimethylethyl (3-pyrrolidinyl)carbamate which solidified upon standing and was of sufficient purity to be used as is for the ensuing steps.

Workup

  1. customThe catalyst was removed
  2. filtrationby filtering through Celite
  3. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-12e2b3393e3c451bbe739415c0d771cd
Source dataset
uspto-grants-1985_10
Patent number
US04550104

Reaction notes

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