Allyl iodide → HCID 131727873, compound

HRID 1441514Notes

Reaction equation

HRID 1441514 reaction equation
[CH3:1][N:2]1[C@@H:12]2[CH2:13][C:14]3[CH:19]=[CH:18][C:17]([OH:20])=[C:16]4[O:21][C@H:6]5[C:7]([CH2:9][CH2:10][C@:11]2([O:22][CH3:23])[C@:5]5([C:15]=34)[CH2:4][CH2:3]1)=[O:8].[CH2:24]([I:27])[CH:25]=[CH2:26]>CN(C)C=O>[I-:27].[CH2:24]([N@+:2]1([CH3:1])[CH2:3][CH2:4][C@:5]23[C:15]4[C:16]5[O:21][C@H:6]2[C:7](=[O:8])[CH2:9][CH2:10][C@@:11]3([O:22][CH3:23])[C@H:12]1[CH2:13][C:14]=4[CH:19]=[CH:18][C:17]=5[OH:20])[CH:25]=[CH2:26]

Participants

4

Reactant 2

HCID 11166Allyl iodideHCID 1355932514-Methoxydihydromorphinone

Product 1

HCID 131727873HCID 131727873, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 14-O-methyloxymorphone (Schmidhammer et al., J. Med. Chem. 1984, 27, pp. 1575-1579) (210 mg, 0.67 mmol) and allyl iodide (0.28 ml, 3.35 mmol) was stirred in 5 ml N,N-dimethylformamide for 7 days at 40° C. (bath temperature) and then evaporated down. The evaporation residue (484 mg of brown oil) was purified using column chromatography (silica gel; CH2Cl2/MeOH (250:5->250:12)). The evaporation residue (134 mg) was again purified using column chromatography (silica gel; CH2Cl2/MeOH (250:4.5)). Evaporation residue 77 mg (27%) of amorphous compound 43. Fp. >140° C.; IR (KBr): 1724 (CO) cm−1; 1H-NMR (DMSO-d6): δ 9.57 (s, C3-OH), 6.68 (s, 2 arom. H), 6.28-6.08 (m, 1 olef. H), 5.75-5.63 (m, 2 olef. H), 4.95 (s, C5-H), 3.42 (s, CH3O), 3.05 (s, +NCH3, equatorial); MS (CI): m/z 356 (M+).

Workup

  1. customevaporated down
  2. customThe evaporation residue (484 mg of brown oil) was purified
  3. customThe evaporation residue (134 mg) was again purified
  4. customEvaporation residue 77 mg (27%) of amorphous compound 43
  5. custom>140° C.

Sources & evidence

ORD record
ord-f23cab38fd7047e9b520fccb359ee2ce
Source dataset
uspto-grants-2010_02
Patent number
US07655671B2

Reaction notes

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