Dimethylformamide → 17alpha,19-Dihydroxy-6-methyl-4,6-pregnadiene-3,20-dione

HRID 894643Notes

Reaction equation

[CH3:1][C:2]1[C:22]2=[CH:23][C:24]([CH2:26][CH2:27][C@:21]2(C)[C@H:5]2[CH2:6][CH2:7][C@:8]3([CH3:20])[C@@:12]([O:16]C(C)=O)([C:13]([CH3:15])=[O:14])[CH2:11][CH2:10][C@H:9]3[C@@H:4]2[CH:3]=1)=[O:25].CN(C)[CH:31]=[O:32]>>[OH:16][C@:12]1([C@:8]2([CH3:20])[C@H:9]([C@H:4]3[C@H:5]([CH2:6][CH2:7]2)[C@:21]2([CH2:31][OH:32])[C:22](=[CH:23][C:24](=[O:25])[CH2:26][CH2:27]2)[C:2]([CH3:1])=[CH:3]3)[CH2:10][CH2:11]1)[C:13](=[O:14])[CH3:15]

Participants

Reactant 2

HCID 6228Dimethylformamide

HCID 11683Megestrol Acetate

Product 1

HCID 5407538417alpha,19-Dihydroxy-6-methyl-4,6-pregnadiene-3,20-dione

Procedure

Under the conditions of Example 1, 10 g. of megestrol (17α-hydroxy-6-methyl-4,6-pregnadiene-3,20-dione), dissolved in 400 ml. of dimethylformamide, is fermented for 48 hours with a Nigrospora sphaerica culture. After the batch has been worked up and the crude product crystallized from acetone/diisopropyl ether, 6.5 g. of 17α,19-dihydroxy-6-methyl-4,6-pregnadiene-3,20-dione is obtained, m.p. 184°-186° C.

Workup

customthe crude product crystallized from acetone/diisopropyl ether, 6.5 g

Sources & evidence

ORD record: ord-cc8d553e346346e8a03f7e81dd6502f7
Source dataset: uspto-grants-1981_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04284720

Reaction notes

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