Water → 3beta-(2,3-Dihydroxypropoxy)-17beta-(3-furyl)-5beta-androstan-14beta-ol

HRID 1647635Notes

Reaction equation

HRID 1647635 reaction equation
C[N+]1([O-])CC[O:5]CC1.[OH2:9].[CH2:10]([O:13][C@H:14]1[CH2:31][CH2:30][C@@:29]2([CH3:32])[C@H:16]([CH2:17][CH2:18][C@@H:19]3[C@@H:28]2[CH2:27][CH2:26][C@@:24]2([CH3:25])[C@:20]3([OH:38])[CH2:21][CH2:22][C@@H:23]2[C:33]2[CH:37]=[CH:36][O:35][CH:34]=2)[CH2:15]1)[CH:11]=[CH2:12].S(S([O-])=O)([O-])=O.[Na+].[Na+]>C(O)(C)(C)C.[Os](=O)(=O)(=O)=O.CC(C)=O>[OH:9][CH:11]([CH2:12][OH:5])[CH2:10][O:13][C@H:14]1[CH2:31][CH2:30][C@@:29]2([CH3:32])[C@H:16]([CH2:17][CH2:18][C@@H:19]3[C@@H:28]2[CH2:27][CH2:26][C@@:24]2([CH3:25])[C@:20]3([OH:38])[CH2:21][CH2:22][C@@H:23]2[C:33]2[CH:37]=[CH:36][O:35][CH:34]=2)[CH2:15]1

Participants

8

Reactant 4

HCID 962WaterHCID 24489Sodium DithioniteHCID 82029Methyl morpholine oxideHCID 228545783beta-Prop-2-enoxy-17beta(3-furyl)-5beta-androstan-14beta-ol

Product 1

HCID 700458923beta-(2,3-Dihydroxypropoxy)-17beta-(3-furyl)-5beta-androstan-14beta-ol

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 180AcetoneSolventHCID 6386tert-ButanolSolvent

Procedure

To a mixture of 0.70 g of N-Methylmorpholine-N-oxide, 6.5 ml of water, 13.7 ml of acetone and 1.64 ml of a 0.06 M ethereal osmium tetroxide solution, 2.0 g of 3β-prop-2-enoxy-17β(3-furyl)-5β-androstan-14β-ol, prepared as an intermediate in Ex.2, dissolved in 29 ml of tert-butanol were added at room temperature. The mixture was left on standing for 20 hrs, 50 ml of a saturated sodium hydrosulfite solution and 2.0 g of celite were added, the mixture was stirred for 2 hrs and then filtered. The organic solvent was distilled under reduced pressure, the aqueous phase was extracted with methylene chloride, the organic layer was dried over anhydrous sodium sulfate and evaporated to dryness under reduced pressure. The crude product was purified by flash-chromatography (SiO2) using n-hexane/ethyl acetate 20/80 as eluant to give 1.8 g of 3β-(2,3-dihydroxypropoxy)-17β-(3-furyl)-5β-androstan-14β-ol as a white solid.

Workup

  1. customprepared as an intermediate in Ex.2
  2. additionwere added at room temperature
  3. waitThe mixture was left
  4. filtrationfiltered
  5. distillationThe organic solvent was distilled under reduced pressure
  6. extractionthe aqueous phase was extracted with methylene chloride
  7. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  8. customevaporated to dryness under reduced pressure
  9. customThe crude product was purified by flash-chromatography (SiO2)

Sources & evidence

ORD record
ord-0aa1e0a9a62946d5a3d8ec2c8d26f0f5
Source dataset
uspto-grants-1995_07
Patent number
US05432169

Reaction notes

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