19-Hydroxy-6alpha-methyl-4-androstene-3,17-dione → 6alpha-Methyl-4-androstene-3alpha,17beta,19-triol

HRID 371836Notes

Reaction equation

HRID 371836 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@H:9]([CH3:22])[C:8]1=[CH: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@@H:9]1[C:8]2[C@:3]([CH2:2][OH:1])([CH2:4][CH2:5][C@@H:6]([OH:23])[CH:7]=2)[C@@H:20]2[C@H:11]([C@H:12]3[C@@:16]([CH2:18][CH2:19]2)([CH3:17])[C@@H:15]([OH:21])[CH2:14][CH2:13]3)[CH2:10]1

Participants

3

Reactant 2

HCID 7058392519-Hydroxy-6alpha-methyl-4-androstene-3,17-dioneHCID 7058499517beta,19-Dihydroxy-7alpha-methyl-4-androstene-3-one

Product 1

HCID 705869436alpha-Methyl-4-androstene-3alpha,17beta,19-triol

Procedure

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

Sources & evidence

ORD record
ord-107cd11134a4479da357c8f3491a0444
Source dataset
uspto-grants-1978_05
Patent number
US04087524

Reaction notes

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