Methyl iodide → HCID 131727875, compound

HRID 1441515Notes

Reaction equation

HRID 1441515 reaction equation
[CH3:1][N:2]1[C@@H:12]2[CH2:13][C:14]3[CH:19]=[CH:18][C:17]([OH:20])=[C:16]4[O:21][C@H:6]5[C:7]([CH2:9][CH2:10][C@:11]2([O:22][CH3:23])[C@:5]5([C:15]=34)[CH2:4][CH2:3]1)=[O:8].[CH3:24][I:25]>C(#N)C>[I-:25].[O:21]1[C@@H:6]2[C@@:5]34[CH2:4][CH2:3][N+:2]([CH3:24])([CH3:1])[C@@H:12]([C@:11]3([O:22][CH3:23])[CH2:10][CH2:9][C:7]2=[O:8])[CH2:13][C:14]2=[C:15]4[C:16]1=[C:17]([OH:20])[CH:18]=[CH:19]2

Participants

4

Reactant 2

HCID 6328Methyl iodide2×HCID 1355932514-Methoxydihydromorphinone

Product 1

HCID 131727875HCID 131727875, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 14-O-methyloxymorphone (Schmidhammer et al., J. Med. Chem. 1984, 27, pp. 1575-1579) (200 mg, 0.63 mmol) and methyl iodide (0.32 ml, 5.07 mmol) in acetonitrile (10 ml) was stirred for 21 hours under N2 at 50° C. (bath temperature). Then methyl iodide (0.2 ml, 3.17 mmol) was again added, stirred further for 24 h under the same conditions and evaporated down. The evaporation residue (324 mg of brown foamy resin) was crystallised out of MeOH (0.5 ml) and purified by recrystallisation out of MeOH. Yield: 244 mg (84%) of compound 44. Fp. 225-240° C.; IR (KBr): 1725 (C═O) cm−1; 1H-NMR (DMSO-d6): δ 9.55 (s, C3—OH), 6.69 (s, 2 arom. H, C1—H, C2—H), 4.94 (s, C5—H), 3.55 (s, +NCH3, axial), 3.38 (s, OCH3), 3.22 (s, +NCH3, equatorial); MS (CI): m/z 330 (M+).

Workup

  1. customevaporated down
  2. customThe evaporation residue (324 mg of brown foamy resin) was crystallised out of MeOH (0.5 ml)
  3. custompurified by recrystallisation out of MeOH
  4. custom225-240° C.

Sources & evidence

ORD record
ord-b8751786294d418fa567ed588456afcf
Source dataset
uspto-grants-2010_02
Patent number
US07655671B2

Reaction notes

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