1-Acetoxy-3-methoxyestra-1,3,5(10)-trien-17-one → 1-Acetoxy-3-methoxyestra-1,3,5(10)-trien-17beta-ol

HRID 839746Notes

Reaction equation

HRID 839746 reaction equation
[C:1]([O:4][C:5]1[C:22]2[C@@H:21]3[C@H:12]([C@H:13]4[C@@:17]([CH2:19][CH2:20]3)([CH3:18])[C:16](=[O:23])[CH2:15][CH2:14]4)[CH2:11][CH2:10][C:9]=2[CH:8]=[C:7]([O:24][CH3:25])[CH:6]=1)(=[O:3])[CH3:2]>C(O)C.O=[Pt]=O>[C:1]([O:4][C:5]1[C:22]2[C@@H:21]3[C@H:12]([C@H:13]4[C@@:17]([CH2:19][CH2:20]3)([CH3:18])[C@@H:16]([OH:23])[CH2:15][CH2:14]4)[CH2:11][CH2:10][C:9]=2[CH:8]=[C:7]([O:24][CH3:25])[CH:6]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 544622991-Acetoxy-3-methoxyestra-1,3,5(10)-trien-17-one

Product 1

HCID 706142631-Acetoxy-3-methoxyestra-1,3,5(10)-trien-17beta-ol

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

A solution of 1-acetoxy-3-methoxyestra-1,3,5(10)-trien-17-one (4.9 g, 14.3 mM) in 250 ml of ethanol is shaken with PtO2 (1 g) under N2 at 40 psi for 7 hrs. After filtration and evaporation of the solvent in vacuo, the oily residue is chromatographed on 250 g of neutral silica gel, initially eluting with benzene and finally progressing to 5% ethyl acetate:benzene. Evaporation of the solvent in vacuo, followed by recrystallization from ether:hexane gives 1-acetoxy-3-methoxyestra-1,3,5(10)-trien-17β-ol, yield 2.35 g (48%), m.p. 107°-110° C.

Workup

  1. filtrationAfter filtration and evaporation of the solvent in vacuo
  2. customthe oily residue is chromatographed on 250 g of neutral silica gel
  3. washinitially eluting with benzene
  4. customEvaporation of the solvent in vacuo
  5. customfollowed by recrystallization from ether

Sources & evidence

ORD record
ord-79e24b75c33b4811ac7668a8a3e76a5d
Source dataset
uspto-grants-1978_06
Patent number
US04096253

Reaction notes

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