HCID 68616384, compound → HCID 10682589, compound

HRID 1893661Notes

Reaction equation

HRID 1893661 reaction equation
[CH3:1][O:2][C:3]([C:5]1([NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:7][CH:6]1[CH2:8][CH:9]=[CH2:10])=[O:4]>CCOC(C)=O.[Rh]>[CH3:1][O:2][C:3]([C:5]1([NH:11][C:12]([O:14][C:15]([CH3:16])([CH3:18])[CH3:17])=[O:13])[CH2:7][CH:6]1[CH2:8][CH2:9][CH3:10])=[O:4]

Participants

4

Reactant 1

HCID 68616384HCID 68616384, compound

Product 1

HCID 10682589HCID 10682589, compound

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-allyl-1-tert-butoxycarbonylamino-cyclopropanecarboxylic acid methyl ester (0.27 mmol) in EtOAc (3 mL) was treated with 5% Rh/Al2O3 (0.014 mmol Rh). The atmosphere over the reaction was replaced with a H2 balloon and the reaction allowed to stir vigorously for 45 min. The H2 was removed and the catalyst removed by filtration through a pad of celite. Volatiles were removed in vacuo to afford 1-tert-butoxycarbonylamino-2-propyl-cyclopropanecarboxylic acid methyl ester as a colorless film that was used without further purification (0.069 g, quant). LCMS found 257.8 [M+H]+

Workup

  1. customThe H2 was removed
  2. customthe catalyst removed by filtration through a pad of celite
  3. customVolatiles were removed in vacuo

Sources & evidence

ORD record
ord-01561ff9eecd463e8559477f43d7b505
Source dataset
uspto-grants-2013_08
Patent number
US08513186B2

Reaction notes

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