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 483782Notes

Reaction equation

HRID 483782 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-butoxycarbonyl)-8-azabicyclo[3.2.1]octa-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-butoxycarbonyl)-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-8c834dc447be43f98e48f875e659a910
Source dataset
uspto-grants-1993_07
Patent number
US05227385

Reaction notes

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