HCID 17039450, compound → HCID 21074825, compound

HRID 1171577Notes

Reaction equation

HRID 1171577 reaction equation
[O:1]=[C:2]1[C@@H:8]2[CH2:9][C@@H:4]([CH2:5][CH2:6][C@@H:7]2[NH:10]C(=O)OCC2C=CC=CC=2)[O:3]1>C(OCC)(=O)C.[Pd]>[NH2:10][C@H:7]1[CH2:6][CH2:5][C@@H:4]2[CH2:9][C@H:8]1[C:2](=[O:1])[O:3]2

Participants

4

Reactant 1

HCID 17039450HCID 17039450, compound

Product 1

HCID 21074825HCID 21074825, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of benzyl (1R,2S,5R)-7-oxo-6-oxa-bicyclo[3.2.1]octan-2-ylcarbamate (20 g, 72.6 mmol) in ethyl acetate (125 mL) was treated with 1.3 g of 10% Pd/C and hydrogenated overnight at 55 psi of H2 in a Parr shaker overnight. The catalyst was filtered and the filtrate concentrated in vacuo to give 10.2 g (100%) of (1R,2S,5R)-2-amino-6-oxa-bicyclo[3.2.1]octan-7-one as an oil. This was used without further purification. MS found: (M+H)+=142.06.

Workup

  1. filtrationThe catalyst was filtered
  2. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-0284a8f5a4a54e44821e813a4d953f67
Source dataset
uspto-grants-2010_11
Patent number
US07829571B2

Reaction notes

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