Methyl iodide → HCID 86600280, compound

HRID 1441512Notes

Reaction equation

HRID 1441512 reaction equation
[O:1]1[C@@H:13]2[C@@:14]34[CH2:16][CH2:17][N:18]([CH3:19])[C@@H:8]([C@:9]3([O:21][CH2:22][CH2:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH2:10][CH2:11][C:12]2=[O:20])[CH2:7][C:6]2=[C:15]4[C:2]1=[C:3]([OH:31])[CH:4]=[CH:5]2.[CH3:32][I:33]>C(#N)C>[I-:33].[O:1]1[C@@H:13]2[C@@:14]34[CH2:16][CH2:17][N+:18]([CH3:32])([CH3:19])[C@@H:8]([C@:9]3([O:21][CH2:22][CH2:23][CH2:24][C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH2:10][CH2:11][C:12]2=[O:20])[CH2:7][C:6]2=[C:15]4[C:2]1=[C:3]([OH:31])[CH:4]=[CH:5]2

Participants

4

Reactant 2

HCID 6328Methyl iodide2×HCID 68537530HCID 68537530, compound

Product 1

HCID 86600280HCID 86600280, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 4,5α-epoxy-3-hydroxy-17-methyl-14β-[(3-phenylpropyl)oxy]morphinan-6-one (oil, 257 mg, 0.61 mmol) and methyl iodide (0.38 ml, 6.11 mmol) in acetonitrile (10 ml) was stirred for 2 days at 50° C. (bath temperature) under N2. A DC examination showed that the reaction was not concluded. Therefore further methyl iodide (0.38 ml, 6.11 mmol) was added and the solution stirred further for 3 days under the same conditions. Then the solvent was evaporated off and the evaporation residue (367 mg of yellow foamy resin) was purified using column chromatography (silica gel; CH2Cl2/MeOH (10:1)). Evaporation residue 240 mg (71%) amorphous compound 38. Fp. 164-170° C.; IR (KBr): 1723 (C═O) cm−1; 1H-NMR (DMSO-d6): δ 9.57 (s, C3-OH), 7.3-7.16 (m, 5 arom. H), 6.67 (s, 2 arom. H, C1—H, C2—H), 4.88 (s, C5—H), 3.56 (s, N+CH3, axial), 3.21 (s, +NCH3, equatorial); MS (CI): m/z 434 (M+).

Workup

  1. customThen the solvent was evaporated off
  2. customthe evaporation residue (367 mg of yellow foamy resin) was purified
  3. customEvaporation residue 240 mg (71%)
  4. custom164-170° C.

Sources & evidence

ORD record
ord-75fdde330b654b5293fd90e047bc575d
Source dataset
uspto-grants-2010_02
Patent number
US07655671B2

Reaction notes

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