Methyl iodide → 17(R)-4,5alpha-epoxy-3-hydroxy-14beta-methoxy-17-methyl-6-oxo-17-(2-phenylethyl)morphinanium-iodide

HRID 1441520Notes

Reaction equation

HRID 1441520 reaction equation
[O:1]1[C@@H:13]2[C@@:14]34[CH2:16][CH2:17][N:18]([CH2:19][CH2:20][C:21]5[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=5)[C@@H:8]([C@:9]3([O:28][CH3:29])[CH2:10][CH2:11][C:12]2=[O:27])[CH2:7][C:6]2=[C:15]4[C:2]1=[C:3]([OH:30])[CH:4]=[CH:5]2.[CH3:31][I:32]>O>[I-:32].[O:1]1[C@@H:13]2[C@@:14]34[CH2:16][CH2:17][N@@+:18]([CH3:31])([CH2:19][CH2:20][C:21]5[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=5)[C@@H:8]([C@:9]3([O:28][CH3:29])[CH2:10][CH2:11][C:12]2=[O:27])[CH2:7][C:6]2=[C:15]4[C:2]1=[C:3]([OH:30])[CH:4]=[CH:5]2

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 68537684HCID 68537684, compound

Product 1

HCID 8660028917(R)-4,5alpha-epoxy-3-hydroxy-14beta-methoxy-17-methyl-6-oxo-17-(2-phenylethyl)morphinanium-iodide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 4,5α-epoxy-3-hydroxy-14β-methoxy-17-(2-phenylethyl)morphinan-6-one (0.32 g, 0.7 mmol) and methyl iodide (0.56 g, 3.92 mmol) in 6 ml of water-free acetonitrile was stirred under N2 40° C. (bath temperature) for 2 days and then evaporated down. The residue (0.32 g of brown oil) was purified using column chromatography (silica gel; CH2Cl2/MeOH 250:2). Yield: 0.07 g (16%) of colourless crystals of the compound 52. Fp. 180-181° C.; MS (CI): 420 (M++1); IR (KBr): 1727 (C═O) cm−1; 1H-NMR (D2O, δ in ppm): 7.17-7.14 (m, 5 arom. H), 6.56 (s, 2 arom. H), 5.18 (s, CH-5), 3.64 (s, CH3N+, axial), 3.44 (s, OCH3).

Workup

  1. customevaporated down
  2. customThe residue (0.32 g of brown oil) was purified
  3. custom180-181° C.

Sources & evidence

ORD record
ord-8796a3c0f2f4476eb4c42494b35e5d49
Source dataset
uspto-grants-2010_02
Patent number
US07655671B2

Reaction notes

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