(6R,7R)-7-benzyloxycarbonylamino-2,2-dimethyl-1-aza-3-oxabicyclo[4.2.0]octan-8-one → (6R,7R)-7-amino-2,2-dimethyl-1-aza-3-oxabicyclo[4.2.0]octan-8-one

HRID 851410Notes

Reaction equation

HRID 851410 reaction equation
C(OC([NH:11][C@H:12]1[C:19](=[O:20])[N:18]2[C@@H:13]1[CH2:14][CH2:15][O:16][C:17]2([CH3:22])[CH3:21])=O)C1C=CC=CC=1>C(OCC)(=O)C.[Pd]>[NH2:11][C@H:12]1[C:19](=[O:20])[N:18]2[C@@H:13]1[CH2:14][CH2:15][O:16][C:17]2([CH3:22])[CH3:21]

Participants

4

Reactant 1

HCID 13744719(6R,7R)-7-benzyloxycarbonylamino-2,2-dimethyl-1-aza-3-oxabicyclo[4.2.0]octan-8-one

Product 1

HCID 12804734(6R,7R)-7-amino-2,2-dimethyl-1-aza-3-oxabicyclo[4.2.0]octan-8-oneYield 91.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of (6R,7R)-7-benzyloxycarbonylamino-2,2-dimethyl-1-aza-3-oxabicyclo[4.2.0]octan-8-one (748 mg) and 10% palladium charcoal (180 mg) in ethyl acetate (15 ml) was stirred under a hydrogen atmosphere for 1.5 hours at ambient temperature. The mixture was filtered and the filtrate was evaporated in vacuo to give (6R,7R)-7-amino-2,2-dimethyl-1-aza-3-oxabicyclo[4.2.0]octan-8-one (382 mg) as a crystalline solid.

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-27d0ae686e1443f2a157ec5e49033ffc
Source dataset
uspto-grants-1983_05
Patent number
US04383945

Reaction notes

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