1-Tert-butoxycarbonyl-3-benzyloxycarbonyl-3-azabicyclo[3.2.0]heptane → 1-Tert-butoxycarbonyl-3-azabicyclo[3.2.0]heptane

HRID 1457974Notes

Reaction equation

HRID 1457974 reaction equation
[C:1]([O:5][C:6]([C:8]12[CH2:14][CH2:13][CH:12]1[CH2:11][N:10](C(OCC1C=CC=CC=1)=O)[CH2:9]2)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>CO.[OH-].[Pd+2].[OH-].[C]>[C:1]([O:5][C:6]([C:8]12[CH2:14][CH2:13][CH:12]1[CH2:11][NH:10][CH2:9]2)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 221005281-Tert-butoxycarbonyl-3-benzyloxycarbonyl-3-azabicyclo[3.2.0]heptaneHCID 178418361HCID 178418361, compound

Product 1

HCID 221005211-Tert-butoxycarbonyl-3-azabicyclo[3.2.0]heptaneYield 136.5%

Reagents, catalysts & solvents 2

HCID 178502593HCID 178502593, compoundCatalystHCID 887MethanolSolvent

Procedure

To a solution of 368 mg (1.02 mmol) of 1-tert-butoxycarbonyl-3-benzyloxycarbonyl-3-azabicyclo[3.2.0]heptane in methanol (20 ml) was added 400 mg of 20% palladium hydroxide-carbon, followed by vigorous stirring in an atmosphere of hydrogen gas. After removing insoluble material by filtration through celite, the resulting filtrate was concentrated to give 274.6 mg of the title compound as a crude product.

Workup

  1. customAfter removing insoluble material
  2. filtrationby filtration through celite
  3. concentrationthe resulting filtrate was concentrated

Sources & evidence

ORD record
ord-40870744f1c0487191a012b7498f00be
Source dataset
uspto-grants-1998_12
Patent number
US05849757

Reaction notes

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