1-t-Butoxycarbonyl-3-dibenzylamino-4-methoxypyrrolidine → tert-Butyl 3-amino-4-methoxypyrrolidine-1-carboxylate

HRID 358899Notes

Reaction equation

HRID 358899 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]([O:13][CH3:14])[CH:10]([N:15](CC2C=CC=CC=2)CC2C=CC=CC=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>C(O)C.[Pd]>[NH2:15][CH:10]1[CH:11]([O:13][CH3:14])[CH2:12][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:9]1

Participants

5

Reactant 2

HCID 200671541-t-Butoxycarbonyl-3-dibenzylamino-4-methoxypyrrolidineHCID 178418361HCID 178418361, compound

Product 1

HCID 20067140tert-Butyl 3-amino-4-methoxypyrrolidine-1-carboxylateYield 81.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

0.13 g of 20% w/w palladium-on-carbon was added to a solution of 0.99 g (0.0025 mole) of 1-t-butoxycarbonyl-3-dibenzylamino-4-methoxypyrrolidine dissolved in 15 ml of ethanol, and the mixture was stirred vigorously at 50° C. for 4 hours in an atmosphere of hydrogen. The catalyst was filtered off from the reaction mixture, after which the filtrate was concentrated by evaporation under reduced pressure, to give 0.44 g of 3-amino-1-t-butoxycarbonyl-4-methoxypyrrolidine as a colorless oil.

Workup

  1. filtrationThe catalyst was filtered off from the reaction mixture
  2. concentrationafter which the filtrate was concentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-88cbf2118f9742239fa525e418b3fe76
Source dataset
uspto-grants-1991_03
Patent number
US04997943

Reaction notes

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