Sodium borohydride → HCID 131714351, compound

HRID 464151Notes

Reaction equation

HRID 464151 reaction equation
C([C@@]12[C@@H]3[C@H]([C@H]4[C@@](CC3)(C)C(=O)CC4)CCC1=CC(=O)CC2)=C.C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.[Pb+4].[CH2:40]=[C:41]1[CH:58]([OH:59])[CH2:57][C@@:56]2([CH:60]=[CH2:61])[C:43]([CH2:44][CH2:45][C@@H:46]3[C@@H:55]2[CH2:54][CH2:53][C@@:51]2([CH3:52])[C@H:47]3[CH2:48][CH2:49][C:50]2=[O:62])=[CH:42]1.[BH4-].[Na+]>C(O)(=O)C.C1C=CC=CC=1>[CH2:40]=[C:41]1[C@@H:58]([OH:59])[CH2:57][C@@:56]2([CH:60]=[CH2:61])[C:43]([CH2:44][CH2:45][C@@H:46]3[C@@H:55]2[CH2:54][CH2:53][C@@:51]2([CH3:52])[C@H:47]3[CH2:48][CH2:49][C@@H:50]2[OH:62])=[CH:42]1

Participants

7

Reactant 4

HCID 4311764Sodium borohydrideHCID 14213833HCID 14213833, compoundHCID 18599505HCID 18599505, compoundHCID 178418268HCID 178418268, compound

Product 1

HCID 131714351HCID 131714351, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 241BenzeneSolvent

Procedure

The compound 10β-vinyl-estra-4-ene-3,17-dione described by Halpern et al, cited above is converted to 10β-vinyl-estra-4-ene-2β-ol-3,17-dione acetate by reaction with a molar excess of lead tetraacetate at 60° to 120° C. in acetic acid or under reflux in benzene for a reaction period of from 6 to 15 hours. This can be converted to 3-methylene-10β-vinyl-estra-4-ene-2-ol-17-one, compound 44, by the Wittig reaction. The latter compound may be reduced with sodium borohydride to produce compound 38, 3-methylene-10β-vinyl-estra-4-ene-2β, 17β-diol.

Sources & evidence

ORD record
ord-ba8c6f4158034788b1c47af60c04ee68
Source dataset
uspto-grants-1985_10
Patent number
US04546098

Reaction notes

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