Methanol → HCID 10981608, compound

HRID 375513Notes

Reaction equation

HRID 375513 reaction equation
[CH:1]1([O:4][C@H:5]2[CH2:10][CH2:9][C@H:8]3[C@H:11]4[C@H:21]([CH2:22][CH2:23][C@:6]23[CH3:7])[C@:19]2([CH3:20])[C:14](=[CH:15][C:16](=[O:24])[CH2:17][CH2:18]2)[CH2:13][CH2:12]4)[CH2:3][CH2:2]1.CC(C)([O-])C.[K+].[N+:31]([O-])([O:33]C(C)C)=[O:32].CO>C(Cl)(Cl)Cl>[CH:1]1([O:4][C@H:5]2[CH2:10][CH2:9][C@H:8]3[C@H:11]4[C@H:21]([CH2:22][CH2:23][C@:6]23[CH3:7])[C@:19]2([CH3:20])[C:14](=[C:15]([N+:31]([O-:33])=[O:32])[C:16](=[O:24])[CH2:17][CH2:18]2)[CH2:13][CH2:12]4)[CH2:2][CH2:3]1

Participants

6

Reactant 4

HCID 887MethanolHCID 15575Isopropyl nitrateHCID 10640035HCID 10640035, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 10981608HCID 10981608, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

17β-cyclopropyloxy-androst-4-en-3-one (9.70 g, 29.5 mM), potassium tert-butoxide (7.0 g, 62.4 mM), and isopropyl nitrate (2.99 ml) are reacted by the method of Example 1 to yield 17β-cyclopropyloxy-4-nitroandrost-4-en-3-one, m.p. 137°-38° C. (methanol) IR (CHCl3) , 1695, 1622(m) , 1535, 1373 cm-1MS(CI) 374(100%, M+10, 316(20%, M+1-c-C3H5 -O) 1H-NMR (CDCl3) 0.38-0.61(4H, m), 0.80(3H, s, C18 -Me), 1.29(s, C19 -Me), 3.25-3.33(1H, m, cyclopropyl-CHO), 3.44(1H, t, C17 -H) .

Sources & evidence

ORD record
ord-61f37b3a360640ec8ab1f2f8eb83c580
Source dataset
uspto-grants-1996_01
Patent number
US05486511

Reaction notes

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