Iodoethane → HCID 68535960, compound

HRID 1441508Notes

Reaction equation

HRID 1441508 reaction equation
ClO.[CH2:3]([N:6]1[CH2:25][CH2:24][C@:13]23[C:14]4[C:15]5[O:23][C@H:12]2[C:11](=[O:26])[CH2:10][CH2:9][C@@:8]3([O:27][CH2:28][CH2:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C@H:7]1[CH2:20][C:19]=4[CH:18]=[CH:17][C:16]=5[O:21][CH3:22])[CH:4]=C.C([O-])([O-])=O.[K+].[K+].C(I)C>O>[O:23]1[C@@H:12]2[C@@:13]34[CH2:24][CH2:25][N:6]([CH2:3][CH3:4])[C@@H:7]([C@:8]3([O:27][CH2:28][CH2:29][CH2:30][C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)[CH2:9][CH2:10][C:11]2=[O:26])[CH2:20][C:19]2=[C:14]4[C:15]1=[C:16]([O:21][CH3:22])[CH:17]=[CH:18]2

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 131727870HCID 131727870, compound

Product 1

HCID 68535960HCID 68535960, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 4,5α-epoxy-3-methoxy-14β-[(3-phenylpropyl)oxy]morphinan-6-one hydrochloride (see Example 1) (4.0 g, 8.77 mmol), K2CO3 (8.0 g, 57.89 mmol), ethyl iodide (0.99 ml, 12.40 mmol) and 50 ml of water-free N,N-dimethylformamide was stirred for 5 h under N2 at 80° C. (bath temperature). After filtration from the inorganic residue, the filtrate was evaporated down and the residue (4.7 g of brown oil) was purified using column chromatography (silica gel; CH2Cl2/MeOH/conc. NH4OH: 8 l: (250/2/0.5)); 0.5 l: (250/3/0.5), (250/4/0.5), (250/6/0.5), (250/8/0.5), (250/10/0.5)). The evaporation residue (1.3 g of bright yellow oil) was crystallised out of MeOH. Yield: 1.2 g (30%) of compound 19. Fp. 95-101° C.; IR (KBr): 1719 (C═O) cm−1; 1H-NMR (DMSO-d6): δ 7.30-7.13 (m, 5 arom. H), 6.73 (d, J=8.2 Hz, 1 arom. H), 6.64 (d, J=8.2 Hz, 1 arom. H), 4.76 (s, 1H, C5—H), 3.78 (s, 3H, OCH3), 0.96 (t, 3H, N—CH2—CH3), J=7 Hz); MS (CI): m/z 448 (M++1).

Workup

  1. filtrationAfter filtration from the inorganic residue
  2. customthe filtrate was evaporated down
  3. customthe residue (4.7 g of brown oil) was purified
  4. customThe evaporation residue (1.3 g of bright yellow oil) was crystallised out of MeOH
  5. custom95-101° C.

Sources & evidence

ORD record
ord-c2647818596d4223a6c3ed1d8f9bb6d8
Source dataset
uspto-grants-2010_02
Patent number
US07655671B2

Reaction notes

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