Methyl iodide → HCID 86600287, compound

HRID 1441519Notes

Reaction equation

HRID 1441519 reaction equation
[Cl:1][C:2]1[CH:33]=[CH:32][C:5]([CH2:6][O:7][C@:8]23[C@@H:21]4[N:22]([CH2:25][CH:26]5[CH2:28][CH2:27]5)[CH2:23][CH2:24][C@:13]52[C:14]2[C:15]([O:30][C@H:12]5[C:11](=[O:31])[CH2:10][CH2:9]3)=[C:16]([OH:29])[CH:17]=[CH:18][C:19]=2[CH2:20]4)=[CH:4][CH:3]=1.[CH3:34][I:35]>O>[I-:35].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][O:7][C@:8]23[C@@H:21]4[N@+:22]([CH2:25][CH:26]5[CH2:28][CH2:27]5)([CH3:34])[CH2:23][CH2:24][C@:13]52[C:14]2[C:15]([O:30][C@H:12]5[C:11](=[O:31])[CH2:10][CH2:9]3)=[C:16]([OH:29])[CH:17]=[CH:18][C:19]=2[CH2:20]4)=[CH:32][CH:33]=1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 68539262HCID 68539262, compound

Product 1

HCID 86600287HCID 86600287, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 14β-[(4-chlorobenzyl)oxy]-17-cyclopropylmethyl-4,5α-epoxy-3-hydroxymorphinan-6-one (0.50 g, 1.07 mmol) and methyl iodide (0.76 g, 5.37 mmol) in 8 ml of water-free acetonitrile was stirred under N2 at 40° C. (bath temperature) for 6 days and then evaporated down. The residue (0.56 g of brown oil) was purified using column chromatography (silica gel; CH2Cl2/MeOH 250:4). Yield: 0.07 g (11%) of beige crystals of the compound 51. Fp. 214-219° C.; MS (CI): 480 (M+); IR (KBr): 1733 (C═O) cm−1; 1H-NMR (DMSO-d6 δ in ppm): 9.57 (s, OH), 7.57 (d, 2 arom. H, C14-OCH2Ph—Cl, J=8.6 Hz), 7.48 (d, 2 arom. H, C14-OCH2Ph—Cl, J=8.6 Hz), 6.71 (s, 2 arom. H), 5.10 (s, CH-5), 4.86 (d, 1H, C14-OCH2, J=11.4 Hz), 4.75-4.66 (m, 3H, C14-OCH2 and CH-9), 3.44 (s, CH3N+, axial).

Workup

  1. customevaporated down
  2. customThe residue (0.56 g of brown oil) was purified
  3. custom214-219° C.

Sources & evidence

ORD record
ord-2a93ac7db2a84f099b773b9245ee09c6
Source dataset
uspto-grants-2010_02
Patent number
US07655671B2

Reaction notes

Loading…