Diethyl cyanophosphonate → 3-Cyano-N-(1,1-dimethylethyl)androsta-3,5-diene-17-beta-carboxamide

HRID 1735549Notes

Reaction equation

[C:1]([NH:5][C:6]([C@H:8]1[CH2:13][CH2:12][C@H:11]2[C@H:14]3[C@H:24]([CH2:25][CH2:26][C@:9]12[CH3:10])[C@:22]1([CH3:23])[C:17](=[CH:18][C:19](=O)[CH2:20][CH2:21]1)[CH2:16][CH2:15]3)=[O:7])([CH3:4])([CH3:3])[CH3:2].P([C:36]#[N:37])(OCC)(OCC)=O>>[C:1]([NH:5][C:6]([C@H:8]1[CH2:13][CH2:12][C@H:11]2[C@H:14]3[C@H:24]([CH2:25][CH2:26][C@:9]12[CH3:10])[C@:22]1([CH3:23])[C:17]([CH:18]=[C:19]([C:36]#[N:37])[CH2:20][CH2:21]1)=[CH:16][CH2:15]3)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

Reactant 2

HCID 76257Diethyl cyanophosphonate

HCID 475445(8S,9S,10R,13S,14S,17S)-N-tert-butyl-10,13-dimethyl-3-oxo-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthrene-17-carboxamide

Product 1

HCID 676469513-Cyano-N-(1,1-dimethylethyl)androsta-3,5-diene-17-beta-carboxamide

Procedure

Following a procedure similar to that described in Example 2(c), but using 100 mg of N-t-butyl-3-oxo-4-androstene-17β-carboxamide (prepared as described in Preparation 1), 0.2 ml of diethyl cyanophosphate and 200 mg of a boron trifluoride-diethyl ether complex, 86 mg of the title compound were obtained as a crystalline substance, melting at 198° to 200° C.

Sources & evidence

ORD record: ord-bccf10f2823f46208d701c249013a0cf
Source dataset: uspto-grants-1996_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05536714

Reaction notes

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