Diethyl Ether → (4aR,5R,8aR)-5-[(R)-5-Hydroxy-1,5-dimethyl-hexyl]-4a-methyl-octahydro-naphtalen-1-one

HRID 1075557Notes

Reaction equation

HRID 1075557 reaction equation
[OH:1][C:2]([CH3:21])([CH3:20])[CH2:3][CH2:4][CH2:5][C@H:6]([C@H:8]1[CH2:17][CH2:16][CH2:15][C@@H:14]2[C@:9]1([CH3:19])[CH2:10][CH2:11][CH2:12][C@@H:13]2[OH:18])[CH3:7].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.C(OCC)C>C(Cl)Cl>[OH:1][C:2]([CH3:20])([CH3:21])[CH2:3][CH2:4][CH2:5][C@H:6]([C@H:8]1[CH2:17][CH2:16][CH2:15][C@@H:14]2[C@:9]1([CH3:19])[CH2:10][CH2:11][CH2:12][C:13]2=[O:18])[CH3:7]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 21309359(1S,4aR,5R,8aR)-5-[(R)-5-Hydroxy-1,5-dimethyl-hexyl]-4a-methyl-decahydro-naphtalen-1-olHCID 178418287HCID 178418287, compound

Product 1

HCID 11022791(4aR,5R,8aR)-5-[(R)-5-Hydroxy-1,5-dimethyl-hexyl]-4a-methyl-octahydro-naphtalen-1-oneYield 85.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 104 mg (0.35 mMol) of (1S,4aR,5R,8aR)-5-[(R)-5-Hydroxy-1,5-dimethyl-hexyl]-4a-methyl-decahydro-naphtalen-1-ol in 2 ml of CH2Cl2 are added under stirring 91.5 mg (0.42 mMol) of pyridiniumchlorochromate. The reaction mixture is kept stirring for 4 hours, diethylether is added and the slurry is filtered through Florisil using diethylether as eluant. The residue obtained after evaporation in vacuo is chromatographed over 5 g of silicagel with CH2Cl2 /ethylacetate 9/1 to yield 88 mg (85.5%) of oily pure (4aR,5R,8aR)-5-[(R)-5-Hydroxy-1,5-dimethyl-hexyl]-4a-methyl-octahydro-naphtalen-1-one.

Workup

  1. filtrationthe slurry is filtered through Florisil
  2. customThe residue obtained
  3. customafter evaporation in vacuo
  4. customis chromatographed over 5 g of silicagel with CH2Cl2 /ethylacetate 9/1

Sources & evidence

ORD record
ord-d32d8176ba0f469687ce6058767aade8
Source dataset
uspto-grants-1999_05
Patent number
US05905074

Reaction notes

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