17beta, 19-Dihydroxy-1alpha,7alpha-dimethyl-4-androsten-3-one diacetate → 17beta,19-Dihydroxy-1alpha,7alpha-dimethyl-4-androsten-3-one

HRID 1733117Notes

Reaction equation

HRID 1733117 reaction equation
C(O)(=O)C.C(O)(=O)C.[OH:9][C@H:10]1[CH2:15][CH2:14][C@H:13]2[C@H:16]3[C@H:27]([CH2:28][CH2:29][C@:11]12[CH3:12])[C@:24]1([CH2:25][OH:26])[C:19](=[CH:20][C:21](=[O:31])[CH2:22][C@@H:23]1[CH3:30])[CH2:18][C@H:17]3[CH3:32]>CO.C[O-].[Na+]>[OH:9][C@H:10]1[CH2:15][CH2:14][C@H:13]2[C@H:16]3[C@H:27]([CH2:28][CH2:29][C@:11]12[CH3:12])[C@:24]1([CH2:25][OH:26])[C:19](=[CH:20][C:21](=[O:31])[CH2:22][C@@H:23]1[CH3:30])[CH2:18][C@H:17]3[CH3:32]

Participants

3

Reactant 1

HCID 8673474217beta, 19-Dihydroxy-1alpha,7alpha-dimethyl-4-androsten-3-one diacetate

Product 1

HCID 7058545317beta,19-Dihydroxy-1alpha,7alpha-dimethyl-4-androsten-3-one

Reagents, catalysts & solvents 1

HCID 23694274Sodium methanolate methanolSolvent

Procedure

17β,19-Dihydroxy-1α,7α-dimethyl-4-androsten-3-one diacetate is dissolved under nitrogen in a sodium methoxide methanol solution at 0° C. and stirred at room temperature for about 2 hours. The solution is poured onto water and the solid collected by filtration. Recrystallization of the solid from acetonitrile yields the desired 17β,19-dihydroxy-1α,7α-dimethyl-4-androsten-3-one.

Workup

  1. additionThe solution is poured onto water
  2. filtrationthe solid collected by filtration
  3. customRecrystallization of the solid from acetonitrile

Sources & evidence

ORD record
ord-340f5d17a5e14707818aa36f897cc570
Source dataset
uspto-grants-1980_12
Patent number
US04239681

Reaction notes

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