Methanol → 3beta-Methoxy-5-androsten-17-one

HRID 551834Notes

Reaction equation

HRID 551834 reaction equation
S(O[C@H:12]1[CH2:29][CH2:28][C@@:27]2([CH3:30])[C:14](=[CH:15][CH2:16][C@@H:17]3[C@@H:26]2[CH2:25][CH2:24][C@@:22]2([CH3:23])[C@H:18]3[CH2:19][CH2:20][C:21]2=[O:31])[CH2:13]1)(C1C=CC(C)=CC=1)(=O)=O.[CH3:32][OH:33]>>[CH3:32][O:33][C@H:12]1[CH2:29][CH2:28][C@@:27]2([CH3:30])[C:14](=[CH:15][CH2:16][C@@H:17]3[C@@H:26]2[CH2:25][CH2:24][C@@:22]2([CH3:23])[C@H:18]3[CH2:19][CH2:20][C:21]2=[O:31])[CH2:13]1

Participants

3

Reactant 2

HCID 887MethanolHCID 13251127HCID 13251127, compound

Product 1

HCID 138032603beta-Methoxy-5-androsten-17-one

Procedure

A solution of 3β-tosyloxyandrost-5-ene-17-one (18) (4.0 g. 9.05 mmol) in anhydrous methanol (120 mL) was refluxed for 2 h. The reaction mixture was concentrated under vacuum. On cooling, a white solid 3β-methoxyandrost-5-ene-17-one (19) was obtained. Recrystallization from methanol afforded shining crystals (2.57 g. 94%), m.p. 133-5° C. (lit m.p. 118-120° C. aq. MeOH).

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. temperatureOn cooling

Sources & evidence

ORD record
ord-f4c0605f963e4555b3767842aa74272d
Source dataset
uspto-grants-2011_05
Patent number
US07947846B2

Reaction notes

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