Testosterone → HCID 11121164, compound

HRID 1290306Notes

Reaction equation

HRID 1290306 reaction equation
[CH3:1][C@@:2]12[C@@H:10]([OH:11])[CH2:9][CH2:8][C@H:7]1[C@@H:6]1[CH2:12][CH2:13][C:14]3[C@@:20]([CH3:21])([C@H:5]1[CH2:4][CH2:3]2)[CH2:19][CH2:18][C:16](=[O:17])[CH:15]=3.CC(C)([O-])C.[K+].C([O:31][N+:32]([O-])=[O:33])(C)C>CC(C)=O.CCCCCC>[OH:11][C@H:10]1[CH2:9][CH2:8][C@H:7]2[C@H:6]3[C@H:5]([CH2:4][CH2:3][C@:2]12[CH3:1])[C@:20]1([CH3:21])[C:14](=[C:15]([N+:32]([O-:33])=[O:31])[C:16](=[O:17])[CH2:18][CH2:19]1)[CH2:13][CH2:12]3

Participants

5

Reactant 3

HCID 6013TestosteroneHCID 15575Isopropyl nitrateHCID 23665647Potassium tert-butoxide

Product 1

HCID 11121164HCID 11121164, compound

Reagents, catalysts & solvents 1

HCID 21880519Acetone hexaneSolvent

Procedure

By the method of example 1, testosterone (2.88 g, 10 mM), potassium tert-butoxide (3.40 g, 30 mM) and iso- propylnitrate (1.01 ml) are reacted to yield 17β-hydroxy-4-nitroandrost-4-en-3-one, m.p. 158°-160° C. (acetone-hexane) IR 3533, 1689, 1615(m), 1635 cm-1MS(CI) 334(100%, M+l), 316(50%, M+1-H2 0) 1H-NMR 6 (CDC13) 0.80(3H, S, C1 8-Me), 1.30(s, Clg-Me), 3.66(lH, t, C17 -H). This compound has the following structure: ##STR11##

Sources & evidence

ORD record
ord-9b9e4eb0422a41dc8bde7c5fb1124fa0
Source dataset
uspto-grants-1998_05
Patent number
US05750744

Reaction notes

Loading…