HCID 53907651, compound → HCID 10863877, compound

HRID 2199018Notes

Reaction equation

HRID 2199018 reaction equation
[CH3:1][O:2][C:3](=[O:35])[CH2:4][CH2:5][C@H:6]([C:8]1[C@:25]2([CH3:26])[C@H:11]([C@H:12]3[C@H:22]([CH2:23][CH2:24]2)[C@:20]2([CH3:21])[C:15]([CH2:16][C@@H:17]([O:31][C:32](=[O:34])[CH3:33])[CH2:18][C@@H:19]2[O:27][C:28](=[O:30])[CH3:29])=[CH:14][CH2:13]3)[CH2:10][CH:9]=1)[CH3:7].[H][H]>C(O)C.[Pt]>[CH3:1][O:2][C:3](=[O:35])[CH2:4][CH2:5][C@H:6]([C@@H:8]1[C@:25]2([CH3:26])[C@H:11]([C@H:12]3[C@H:22]([CH2:23][CH2:24]2)[C@:20]2([CH3:21])[C:15]([CH2:16][C@@H:17]([O:31][C:32](=[O:34])[CH3:33])[CH2:18][C@@H:19]2[O:27][C:28](=[O:30])[CH3:29])=[CH:14][CH2:13]3)[CH2:10][CH2:9]1)[CH3:7]

Participants

5

Reactant 2

HCID 53907651HCID 53907651, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 10863877HCID 10863877, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 8.8 g of 1α,3β-diacetyloxychola-5,16-dien-24-oic acid methyl ester in 200 ml of absolute ethanol was added, under a nitrogen atmosphere, 0.8 g of 5% platinum on charcoal. The suspension was then stirred under a hydrogen atmosphere at 23° C. until hydrogen absorption ceased (2.75 h; 423 ml; theory, 437 ml). Filtration through diatomaceous earth did not remove all colloidal particles. The evaporated filtrate was dissolved in 50 ml of ethyl acetate--methylene chloride (1:1) and was then percolated through a column of 20 g of silica gel using the same solvent mixture. Evaporation of the solvents gave 8.7 g (99%) of 1α,3β-diacetyloxychol-5-en-24-oic acid methyl ester as a white solid, mp 108°-113° C. An analytical sample, recrystallized from methanol, had mp 110.5°-112° C.

Workup

  1. custom(2.75 h; 423 ml; theory, 437 ml)
  2. filtrationFiltration through diatomaceous earth
  3. customdid not remove all colloidal particles
  4. dissolutionThe evaporated filtrate was dissolved in 50 ml of ethyl acetate--methylene chloride (1:1)
  5. customEvaporation of the solvents

Sources & evidence

ORD record
ord-453fef930e5f472995c6fa5cb40148f9
Source dataset
uspto-grants-1982_11
Patent number
US04360470

Reaction notes

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