2-Acetyl-3-methyl-8-(tert-butoxycarbonyl)-8-azabicyclo[3.2.1]octa-2,6-diene → 2-Acetyl-3-methyl-8-(tert-butoxycarbonyl)-8-azabicyclo[3.2.1]oct-2-en

HRID 1975819Notes

Reaction equation

HRID 1975819 reaction equation
[C:1]([C:4]1[CH:5]2[N:12]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH:8]([CH2:9][C:10]=1[CH3:11])[CH:7]=[CH:6]2)(=[O:3])[CH3:2].[H][H]>C(O)C>[C:1]([C:4]1[CH:5]2[N:12]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH:8]([CH2:9][C:10]=1[CH3:11])[CH2:7][CH2:6]2)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 197513572-Acetyl-3-methyl-8-(tert-butoxycarbonyl)-8-azabicyclo[3.2.1]octa-2,6-dieneHCID 178418361HCID 178418361, compound

Product 1

HCID 197513552-Acetyl-3-methyl-8-(tert-butoxycarbonyl)-8-azabicyclo[3.2.1]oct-2-en

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-acetyl-3-methyl-8-(tert-butyloxycarbonyl)-8-azabicyclo [3.2.1]oct-2,6-diene (0.74 g, 2.81 mmol) and RhCl(PPh3)3 (0.026 g, 0.028 mmol) in 50 ml ethanol was pressurized with 45 psi hydrogen gas and shaken for about 12 hours. The solvent was then evaporated and the residue was purified by silica gel column chromatography (using 3 parts diethyl ether and 7 parts petroleum ether) to give 2-acetyl-3- methyl-8-(tert-butyloxycarbonyl)-8-azabicyclo [3.2.1]oct-2-en.

Workup

  1. customThe solvent was then evaporated
  2. customthe residue was purified by silica gel column chromatography (using 3 parts diethyl ether and 7 parts petroleum ether)

Sources & evidence

ORD record
ord-30cdc87d15454aab88c7be77b69c744d
Source dataset
uspto-grants-1994_02
Patent number
US05288872

Reaction notes

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