17beta,19-Dihydroxy-7alpha-methyl-5-androsten-3-one → 6-Methyl-5-androstene-3alpha,17beta,19-triol

HRID 1390774Notes

Reaction equation

HRID 1390774 reaction equation
[OH:1][CH2:2][C@@:3]12[C@@H:20]3[C@H:11]([C@H:12]4[C@@:16]([CH2:18][CH2:19]3)([CH3:17])[C:15](=[O:21])[CH2:14][CH2:13]4)[CH2:10][C:9]([CH3:22])=[C:8]1[CH2:7][C:6](=[O:23])[CH2:5][CH2:4]2.O[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@]12C)[C@]1(CO)C(CC(=O)CC1)=C[C@H]3C>>[CH3:22][C:9]1[CH2:10][C@@H:11]2[C@@H:20]([C@:3]3([CH2:2][OH:1])[C:8]=1[CH2:7][C@H:6]([OH:23])[CH2:5][CH2:4]3)[CH2:19][CH2:18][C@@:16]1([CH3:17])[C@H:12]2[CH2:13][CH2:14][C@@H:15]1[OH:21]

Participants

3

Reactant 2

HCID 7060530117beta,19-Dihydroxy-7alpha-methyl-5-androsten-3-oneHCID 7060555919-Hydroxy-6-methyl-5-androstene-3,17-dione

Product 1

HCID 706049966-Methyl-5-androstene-3alpha,17beta,19-triol

Procedure

Substituting 17β,19-dihydroxy-4α,17α-dimethyl-5-androsten-3-one and 19-hydroxy-6-methyl-5-androstene-3,17-dione for the 17β,19-dihydroxy-7α-methyl-5-androsten-3-one above results in the preparation of 4,17α-dimethyl-5-androstene-3α,17β,19-triol and 6-methyl-5-androstene-3α,17β,19-triol, respectively.

Sources & evidence

ORD record
ord-3c5594ec26f24e68b5c544cf947e78af
Source dataset
uspto-grants-1979_02
Patent number
US04139617

Reaction notes

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