Acetic Acid → 2-Methoxy-6a-methyl-4b,6,6a,7,8,8a,9,9b,10,11-decahydro-5H-cyclopropa[1,5]cyclopenta[1,2-a]phenanthren-7-ol

HRID 224237Notes

Reaction equation

HRID 224237 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 11973384HCID 11973384, compound

Product 2

HCID 30359102-Methoxy-6a-methyl-4b,6,6a,7,8,8a,9,9b,10,11-decahydro-5H-cyclopropa[1,5]cyclopenta[1,2-a]phenanthren-7-olHCID 11973409HCID 11973409, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

400 mg of 3-methoxy-14β,15β-methylene-estra-1,3,5(10)-triene-17-one dissolved in 300 ml of methanol are mixed with 380 mg of sodium borohydride at 0° C. and set aside overnight at room temperature. Subsequently the mixture is reduced to half its volume in vacuum and poured into cold aqueous acetic acid. The precipitate is dried, and preparative layer chromatography on silica gel (mobile phase: benzene/acetone 3:2) yields 90 mg of 3-methoxy-14β,15β-methylene-estra-1,3,5(10)-triene-17β-ol and 210 mg of 3-methoxy-14β,15β-methylene-estra-1,3,5(10)-triene-17α-ol. Flash point 117° to 119° C., specific optical rotation: [α]D25 +104.0° (c=1; CHCl3).

Workup

  1. customThe precipitate is dried

Sources & evidence

ORD record
ord-903a76f5c7bc4df697c563d90617db83
Source dataset
uspto-grants-1980_11
Patent number
US04231946

Reaction notes

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