2,3,8a-trimethyl-3,4,4a,5,8,8a-hexahydro-1(2H)-naphthalenone → 2,3,8a-Trimethyloctahydronaphthalen-1(2H)-one

HRID 645334

Reaction equation

HRID 645334 reaction equation
[CH3:1][CH:2]1[CH:11]([CH3:12])[CH2:10][CH:9]2[C:4]([CH3:13])([CH2:5][CH:6]=[CH:7][CH2:8]2)[C:3]1=[O:14]>C(OCC)(=O)C.[Pd]>[CH3:1][CH:2]1[CH:11]([CH3:12])[CH2:10][CH:9]2[C:4]([CH3:13])([CH2:5][CH2:6][CH2:7][CH2:8]2)[C:3]1=[O:14]

Participants

4

Reactant 1

HCID 574294412,3,8a-trimethyl-3,4,4a,5,8,8a-hexahydro-1(2H)-naphthalenone

Product 1

HCID 160635322,3,8a-Trimethyloctahydronaphthalen-1(2H)-oneYield 98.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

2,3,8a-trimethyl-3,4,4a,5,8,8a-hexahydro-1(2H)-naphthalenone (10 g, 52 mmol) was hydrogenated, at room temperature and atmospheric pressure, in ethyl acetate (100 ml) in presence of 5% Pd—C (1.0 g). The crude product was purified by bulb-to-bulb distillation (78° C./0.035 mbar) to give desired compound (9.88 g, 51 mmol, 98%) as a 3:2 mixture of diastereoisomers.

Workup

  1. customwas hydrogenated, at room temperature
  2. distillationThe crude product was purified by bulb-to-bulb distillation (78° C./0.035 mbar)

Sources & evidence

ORD record
ord-e1d4afe416e04b76a6d08fcff7dc2034
Source dataset
uspto-grants-2010_04
Patent number
US07704933B2

Linked notes

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