Tert-Butylamine → (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

HRID 962696Notes

Reaction equation

HRID 962696 reaction equation
[O:1]=[C:2]1[CH2:19][CH2:18][C@@:17]2([CH3:20])[C:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:16]2[CH2:15][CH2:14][C@@:12]2([CH3:13])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C:21](=[O:29])SC2C=CC=CN=2)=[CH:3]1.[C:30]([NH2:34])([CH3:33])([CH3:32])[CH3:31]>>[C:30]([NH:34][C:21]([C@H:11]1[CH2:10][CH2:9][C@H:8]2[C@H:7]3[C@H:16]([CH2:15][CH2:14][C@:12]12[CH3:13])[C@:17]1([CH3:20])[C:4](=[CH:3][C:2](=[O:1])[CH2:19][CH2:18]1)[CH2:5][CH2:6]3)=[O:29])([CH3:33])([CH3:32])[CH3:31]

Participants

3

Reactant 2

HCID 6385Tert-ButylamineHCID 15380261S-2-pyridyl 3-oxo-4-androstene-17beta-thiocarboxylate

Product 1

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

Procedure

Following a procedure similar to that described in Example 2(b), but using 9.77 g of S-2-pyridyl 3-oxo-4-androstene-17β-thiocarboxylate [prepared as described in Example 2(a)] and 14 ml of t-butylamine, 8.9 g of the title compound were obtained.

Sources & evidence

ORD record
ord-6d440e97e4d24fac9be88be14f8d507a
Source dataset
uspto-grants-1998_06
Patent number
US05760025

Reaction notes

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