Reaktion #456185

Reaktionsgleichung

4,5α-epoxy-3-methoxy-5-methyl-14-n-propyloxymorphinan-6-one hydrochloride

4,5α-epoxy-3-methoxy-5-methyl-14-n-propyloxy-morphinan-6-one hydrochloride

compound 12

4,5α-epoxy-3-methoxy-5-methyl-14-n-propyloxy-morphinan-6-one hydrochloride

potassium carbonate

cyclopropylmethyl chloride

→

17-(cydopropylmethyl)-4,5α-epoxy-3-methoxy-5-methyl-14-n-propyloxymorphinan-6-one hydrochloride

Ausbeute 55.4%

Lösungsmittel

N,N-dimethyl formamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   FiltrationThe inorganic solid was filtered off
2. 2
   Sonstigethe filtrate evaporated
3. 3
   WaschenA solution of the residue in 30 ml of CH2Cl2 was washed with H2O (3×30 ml)
4. 4
   Trocknendried over Na2SO4
5. 5
   Sonstigeevaporated
6. 6
   workup.DISSOLUTIONThe residue (1,69 g orange-yellow oil) was dissolved in diethyl ether
7. 7
   workup.ADDITIONtreated with ethereal HCl

Vorschrift

A mixture of 4,5α-epoxy-3-methoxy-5-methyl-14-n-propyloxymorphinan-6-one hydrochloride (compound 12 of Example 7) (1.46 g, 3.71 mmol), potassium carbonate (2.24 g, 16.24 mmol), cyclopropylmethyl chloride (0.43 ml, 4.44 mmol), and 15 ml of anhydrous N,N-dimethyl formamide was stirred at 85° C. (bath temperature) for 36 h. The inorganic solid was filtered off and the filtrate evaporated. A solution of the residue in 30 ml of CH2Cl2 was washed with H2O (3×30 ml), dried over Na2SO4 and evaporated. The residue (1,69 g orange-yellow oil) was dissolved in diethyl ether and treated with ethereal HCl to give 920 mg (55%) of 17-(cydopropylmethyl)-4,5α-epoxy-3-methoxy-5-methyl-14-n-propyloxymorphinan-6-one hydrochloride (compound 16) as colorless powder. M.p. 156-158° C. IR (KBr): 3400 (+NH), 1723 (CO) cm-1. CI-MS: m/z 412 (M+ +1). 1H-MR (DMSO-d6): δ 8.57 (s, +NH), 6,85 (d, J=8.2 Hz, 1 arom. H), 6.75 (d, J=8.2 Hz, 1 rom. H), 3.79 (s, OCH3), 1.51 (s, CH3 --C(5)), 0.97 (t, J=7.4 Hz, CH3). Analysis calculated for C25H33NO4HCl. 0.6 H2O(458.81): C 65.45, H 7.73, N 3.05, Cl 7.73; found: C 65.45, H 7.85, N 3.08, Cl 7.84.

Quelle