Methyl iodide → HCID 86600283, compound

HRID 1441516Notes

Reaction equation

HRID 1441516 reaction equation
[CH2:1]([C@@:8]12[O:33][C:11]3=[C:12]([OH:32])[CH:13]=[CH:14][C:15]4[CH2:16][C@H:17]5[N:28]([CH3:31])[CH2:29][CH2:30][C@:9]1([C@@:18]5([O:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH2:19][CH2:20][C:21]2=[O:22])[C:10]=43)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:34][I:35]>O>[I-:35].[CH2:1]([C@@:8]12[O:33][C:11]3=[C:12]([OH:32])[CH:13]=[CH:14][C:15]4[CH2:16][C@H:17]5[N+:28]([CH3:34])([CH3:31])[CH2:29][CH2:30][C@:9]1([C@@:18]5([O:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH2:19][CH2:20][C:21]2=[O:22])[C:10]=43)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 86600285HCID 86600285, compound

Product 1

HCID 86600283HCID 86600283, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 5β-benzyl-14β-butoxy-4,5α-epoxy-3-hydroxy-17-methylmorphinan-6-one (0.32 g, 0.72 mmol) and methyl iodide (0.51 g, 3.58 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 (0.41 g of brown oil) was purified using column chromatography (silica gel; CH2Cl2/MeOH 250:6). Yield: 0.22 g (54%) slightly beige crystals of the compound 45. Fp. 188-195° C.; MS (CI): 462 (M+); IR (KBr): 1729 (C═O) cm−1; 1H-NMR (DMSO-d6, δ in ppm): 9.49 (s, OH), 7.28-7.20 (m, 5 arom. H), 6.69 (d, 1 arom. H, J=8.2 Hz), 6.62 (d, 1 arom. H, J=8.2 Hz), 3.61 (s, CH3N+, axial), 3.23 (s, CH3N+, equatorial), 1.01 (t, 3H, C14-O(CH2)3CH3, J=7.0 Hz).

Workup

  1. customevaporated down
  2. customThe evaporation residue (0.41 g of brown oil) was purified
  3. custom188-195° C.

Sources & evidence

ORD record
ord-f313ef360bde40159ad2877e2861483a
Source dataset
uspto-grants-2010_02
Patent number
US07655671B2

Reaction notes

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