HCID 20541499, compound → HCID 20541497, compound

HRID 1065141Notes

Reaction equation

HRID 1065141 reaction equation
[O:1]=[C:2]1[CH2:11][CH2:10][C:9]2([OH:12])[C:4]3([CH3:16])[CH:5]=[CH:6][CH:7]([CH2:15][CH:3]13)[C:8]2([CH3:14])[CH3:13]>C(O)C.O=[Pt]=O>[O:1]=[C:2]1[CH2:11][CH2:10][C:9]2([OH:12])[C:4]3([CH3:16])[CH2:5][CH2:6][CH:7]([CH2:15][CH:3]13)[C:8]2([CH3:13])[CH3:14]

Participants

4

Reactant 1

HCID 20541499HCID 20541499, compound

Product 1

HCID 20541497HCID 20541497, compoundYield 92.3%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

22 mg of 1,2,3,4,4a,5,6,8a-octahydro-2-oxo-4a-hydroxy-5,5,8a-trimethyl-1,6-methanonaphthalene in 4 ml of ethanol is stirred in the presence of 6 mg of PtO2 for 12 hours under a H2 atmosphere (1 atm, 25° C.). The reaction mixture, filtered through Celite and evaporated, gave, after chromatography and sublimation, 20.5 mg of 1,2,3,4,4a,5,6,7,8,8a-decahydro-2-oxo-4a-hydroxy-5,5,8a-trimethyl-1,6-methanonaphthalene (m.p. 120°-123° C., 92% yield).

Workup

  1. filtrationThe reaction mixture, filtered through Celite
  2. customevaporated
  3. customgave

Sources & evidence

ORD record
ord-ae4d4f61b2cd4b7aa434bf3f037dc2ec
Source dataset
uspto-grants-1982_05
Patent number
US04328352

Reaction notes

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