HCID 86744422, compound → HCID 57090419, compound

HRID 1110954Notes

Reaction equation

HRID 1110954 reaction equation
[CH:1](/[C@:11]1([CH3:22])[C@H:18]2[CH2:19][C@H:14]([C@@H:15]([CH3:21])[C:16](=[O:20])[CH2:17]2)[O:13][O:12]1)=[CH:2]\[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[H][H]>C(OCC)(=O)C.[Pt]>[CH2:1]([C@@:11]1([CH3:22])[C@H:18]2[CH2:19][C@H:14]([C@@H:15]([CH3:21])[C:16](=[O:20])[CH2:17]2)[O:13][O:12]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

5

Reactant 2

HCID 86744422HCID 86744422, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 57090419HCID 57090419, compound

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

3.59 g of (1R,4S,5S,8R)-4-[(E)-1-decenyl]-4,8-dimethyl-2,3-dioxabicyclo[3.3.1]nonan-7-one [obtained in accordance with Example 2(e)] dissolved in 180 ml of ethyl acetate are hydrogenated for about 1.25 hours with hydrogen over 360 mg of 5 percent platinum/charcoal at 1.013·105Pa. The end point of the reaction is determined by gas-chromatographic analysis. The catalyst is then removed by filtration through diatomaceous earth and the filtrate is evaporated. The residue is purified by column chromatography on silica gel while eluting with hexane/ethyl acetate (3:1). There is obtained (1R,4S,5S,8R)-4-decyl-4,8-dimethyl-2,3-dioxabicyclo[3.3.1]-nonan-7-one as a colourless oil, which crystallizes from hexane [m.p. 57°].

Workup

  1. customThe catalyst is then removed by filtration through diatomaceous earth
  2. customthe filtrate is evaporated
  3. customThe residue is purified by column chromatography on silica gel
  4. washwhile eluting with hexane/ethyl acetate (3:1)

Sources & evidence

ORD record
ord-a046b4751cbf494ab1e611acfabe8005
Source dataset
uspto-grants-1990_12
Patent number
US04977184

Reaction notes

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