Methyl iodide → HCID 86619016, compound

HRID 1441518Notes

Reaction equation

HRID 1441518 reaction equation
[CH:1]1([CH2:4][N:5]2[CH2:23][CH2:22][C@:12]34[C:13]5[C:14]6[O:21][C@H:11]3[C:10](=[O:24])[CH2:9][CH2:8][C@@:7]4([O:25][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[C@H:6]2[CH2:19][C:18]=5[CH:17]=[CH:16][C:15]=6[OH:20])[CH2:3][CH2:2]1.[CH3:39][I:40]>O>[I-:40].[CH:1]1([CH2:4][N@@+:5]2([CH3:39])[CH2:23][CH2:22][C@:12]34[C:13]5[C:14]6[O:21][C@H:11]3[C:10](=[O:24])[CH2:9][CH2:8][C@@:7]4([O:25][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[C@H:6]2[CH2:19][C:18]=5[CH:17]=[CH:16][C:15]=6[OH:20])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 68538283HCID 68538283, compound

Product 1

HCID 86619016HCID 86619016, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 17-cyclopropylmethyl-4,5α-epoxy-3-hydroxy-14β-[(2-phenylbenzyl)oxy]morphinan-6-one (0.39 g, 0.76 mmol) and methyl iodide (0.54 g, 3.79 mmol) in 6 ml of water-free acetonitrile was stirred under N2 at 40° C. (bath temperature) for 2 days and then evaporated down. The residue (0.5 g of brown oil) was purified using column chromatography (silica gel; CH2Cl2/MeOH 250:4). Yield: 0.02 g (4%) of beige crystals of the compound 50. Fp. 219-221° C.; MS (CI): 522 (M+); IR (KBr): 1725 (C═O) cm−1; 1H-NMR (DMSO-d6): δ 9.53 (s, OH), 7.68-7.25 (m, 9 arom. H), 6.67 (s, 2 arom. H), 4.73 (d, C14-OCH2), 4.61 (s, CH-5), 3.26 (s, CH3N+, axial).

Workup

  1. customevaporated down
  2. customThe residue (0.5 g of brown oil) was purified
  3. custom219-221° C.

Sources & evidence

ORD record
ord-ca25c9b711b24de486f1602dbfcd406b
Source dataset
uspto-grants-2010_02
Patent number
US07655671B2

Reaction notes

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