Acetic Acid → 17-hydroxy-3-methoxy-14,15-methylenestra-1,3,5(a)-trien

HRID 224238Notes

Reaction equation

HRID 224238 reaction equation
[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:18]2[C@@H:17]3[C@H:8]([C@:9]45[CH2:22][C@H:10]4[CH2:11][C:12](=[O:21])[C@:13]5([CH2:15][CH2:16]3)[CH3:14])[CH2:7][CH2:6][C:5]=2[CH:4]=1.[BH4-].[Na+].C(O)(=O)C>CO>[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:18]2[C@@H:17]3[C@H:8]([C@:9]45[CH2:22][C@H:10]4[CH2:11][C@@H:12]([OH:21])[C@:13]5([CH2:15][CH2:16]3)[CH3:14])[CH2:7][CH2:6][C:5]=2[CH:4]=1.[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:18]2[C@@H:17]3[C@H:8]([C@:9]45[CH2:22][C@H:10]4[CH2:11][C@H:12]([OH:21])[C@:13]5([CH2:15][CH2:16]3)[CH3:14])[CH2:7][CH2:6][C:5]=2[CH:4]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 11130234HCID 11130234, compound

Product 2

HCID 17323317-hydroxy-3-methoxy-14,15-methylenestra-1,3,5(a)-trienHCID 11022909HCID 11022909, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

400 mg of 3-methoxy-14α,15α-methylene-estra-1,3,5(10)-triene-17-one dissolved in 150 ml of methanol are mixed with 400 mg of sodium borohydride at 0° C. and set aside overnight at room temperature. The mixture is poured into cold aqueous acetic acid. The precipitate is dried and preparative layer chromatography on silica gel (mobile phase: benzene/acetone/methanol 45:5:1) yields 180 mg of 3-methoxy-14α,15α-methylene-estra-1,3,5(10)-triene-17α-ol and 220 mg of 3-methoxy-14α,15α-methylene-estra-1,3,5(10)-triene-17β-ol.

Workup

  1. customThe precipitate is dried

Sources & evidence

ORD record
ord-ef02689505524e5ab1b607a041e89833
Source dataset
uspto-grants-1980_11
Patent number
US04231946

Reaction notes

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