HCID 12851175, compound → HCID 12790110, compound

HRID 1105843Notes

Reaction equation

HRID 1105843 reaction equation
[C:1]([O:4][C@@H:5]1[C@@:25]2([CH3:26])[C:9](=[CH:10][CH2:11][C@@H:12]3[C@@H:24]2[CH2:23][CH2:22][C@@:21]2([CH3:27])[C@H:13]3[CH2:14][CH:15]=[C:16]2[C@H:17]([CH3:20])[CH2:18][OH:19])[CH2:8][C@@H:7]([O:28][C:29](=[O:31])[CH3:30])[CH2:6]1)(=[O:3])[CH3:2].[H][H]>C(O)C.[Pt]>[C:1]([O:4][C@@H:5]1[C@@:25]2([CH3:26])[C:9](=[CH:10][CH2:11][C@@H:12]3[C@@H:24]2[CH2:23][CH2:22][C@@:21]2([CH3:27])[C@H:13]3[CH2:14][CH2:15][C@@H:16]2[C@H:17]([CH3:20])[CH2:18][OH:19])[CH2:8][C@@H:7]([O:28][C:29](=[O:31])[CH3:30])[CH2:6]1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 12851175HCID 12851175, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 12790110HCID 12790110, compoundYield 86.2%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 860 mg (2.0 mmol) of (20S)-20-methylpregna-5,16-diene-1α,3β,21-triol 1,3-diacetate in 50 ml of absolute ethanol was added 89 mg of 5% platinum on charcoal. The suspension was stirred under a hydrogen atmosphere at 23° until (2 hr.) the hydrogen uptake was 48 ml (theory 48.8 ml). The catalyst was removed by filtration (several filtrations were necessary to remove colloidal charcoal) through diatomaceous earth and was washed several times with methylene chloride. The filtrate was evaporated under reduced pressure, and the residue, 835 mg (97%), was recrystallized from 20 ml of hexane (cooled to -5°) to yield 746 mg (86%) of (20S)-20-methylpregn-5-ene-1α,3β,21-triol 1,3-diacetate as white crystals, mp 133.5°-134.5°.

Workup

  1. customThe catalyst was removed by filtration (several filtrations were necessary to remove colloidal charcoal) through diatomaceous earth
  2. washwas washed several times with methylene chloride
  3. customThe filtrate was evaporated under reduced pressure
  4. customthe residue, 835 mg (97%), was recrystallized from 20 ml of hexane (cooled to -5°)

Sources & evidence

ORD record
ord-99694f5a7868486da7b79b4bc4f4e007
Source dataset
uspto-grants-1982_01
Patent number
US04310467

Reaction notes

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