HCID 69788899, compound → HCID 9795964, compound

HRID 1815774Notes

Reaction equation

HRID 1815774 reaction equation
C[O:2][C:3]1[CH:20]=[CH:19][C:18]2[C@@H:17]3[C@H:8]([C@@H:9]4[C@@:13]([CH2:15][CH2:16]3)([CH3:14])[C@H:12]([CH2:21][OH:22])[CH2:11][CH2:10]4)[CH2:7][CH2:6][C:5]=2[CH:4]=1.COC1CC2CC[C@@H]3[C@@H](C=2CC=1)CC[C@@]1(C)[C@@H]3CC[C@H]1CO>>[OH:22][CH2:21][C@@H:12]1[CH2:11][CH2:10][C@@H:9]2[C@H:8]3[C@H:17]([CH2:16][CH2:15][C@:13]12[CH3:14])[C@@H:18]1[C:5](=[CH:4][C:3](=[O:2])[CH2:20][CH2:19]1)[CH2:6][CH2:7]3

Participants

3

Reactant 2

HCID 69788899HCID 69788899, compoundHCID 69790361HCID 69790361, compound

Product 1

HCID 9795964HCID 9795964, compound

Procedure

Birch reduction of the (14β,17α)-3-methoxyestra-1,3,5(10)-triene-17-methanol derivatives thus obtained [Caine, D. in Org. Reactions 23, p. 1, Wiley, New York, 1976] and hydrolysis of the resulting (14β,17α)-3-methoxyestra-2,5(10)-diene-17-methanol derivative then provides a (14β,17α)-17-(hydroxymethyl)estr-4-en-3-one derivative of the invention.

Sources & evidence

ORD record
ord-5e1543bbc52c4c4c83a7b0123baefe77
Source dataset
uspto-grants-2005_04
Patent number
US06881728B1

Reaction notes

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