Methyl iodide → HCID 86600286, compound

HRID 1441517Notes

Reaction equation

HRID 1441517 reaction equation
[CH2:1]([O:5][C@:6]12[C@@H:19]3[N:20]([CH3:23])[CH2:21][CH2:22][C@:11]41[C:12]1[C:13]([O:25][C@H:10]4[C:9](=[O:26])[CH2:8][CH2:7]2)=[C:14]([OH:24])[CH:15]=[CH:16][C:17]=1[CH2:18]3)[CH2:2][CH2:3][CH3:4].[CH3:27][I:28]>O>[I-:28].[CH2:1]([O:5][C@:6]12[C@@H:19]3[N+:20]([CH3:27])([CH3:23])[CH2:21][CH2:22][C@:11]41[C:12]1[C:13]([O:25][C@H:10]4[C:9](=[O:26])[CH2:8][CH2:7]2)=[C:14]([OH:24])[CH:15]=[CH:16][C:17]=1[CH2:18]3)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 56653640HCID 56653640, compound

Product 1

HCID 86600286HCID 86600286, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 14β-butoxy-4,5α-epoxy-3-hydroxy-17-methylmorphinan-6-one (0.53 g, 1.49 mmol) and methyl iodide (1.06 g, 7.44 mmol) in 10 ml of water-free acetonitrile was stirred under N2 at 40° C. (bath temperature) for 2 days and then evaporated down. The evaporation residue (0.70 g of brown oil) was purified using column chromatography (silica gel; CH2Cl2/MeOH 250:4). Yield: 0.31 g (42%) of colourless crystals of the compound 47. Fp. 180-185° C.; MS (CI): 372.2 (M+); IR (KBr): 1726 (C═O) cm−1; 1H-NMR (DMSO-d6, δ in ppm): 9.55 (s, OH), 6.68 (s, 2 arom. H), 4.95 (s, CH-5), 3.57 (s, CH3N+, axial), 3.21 (s, CH3N+, equatorial), 0.94 (t, O(CH2)3CH3, J=7.3 Hz).

Workup

  1. customevaporated down
  2. customThe evaporation residue (0.70 g of brown oil) was purified
  3. custom180-185° C.

Sources & evidence

ORD record
ord-d1a3b0cfd9414d7ab92dff00c3dc803a
Source dataset
uspto-grants-2010_02
Patent number
US07655671B2

Reaction notes

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