Methyl iodide → HCID 69300194, compound

HRID 2252387Notes

Reaction equation

HRID 2252387 reaction equation
[CH:1]1([CH2:4][N:5]2[CH2:26][CH2:25][C@:12]34[C:13]5[C:14]6[O:24][C@H:11]3[CH:10]([N:27]3[C:31](=[O:32])[C:30]7=[C:33]([OH:37])[CH:34]=[CH:35][CH:36]=[C:29]7[C:28]3=[O:38])[CH2:9][CH2:8][C@@:7]4([OH:39])[C@H:6]2[CH2:19][C:18]=5[CH:17]=[CH:16][C:15]=6[O:20][CH2:21][O:22][CH3:23])[CH2:3][CH2:2]1.[C:40](=O)([O-])[O-].[K+].[K+].CI.C(=O)([O-])O.[Na+]>CN(C=O)C>[CH:1]1([CH2:4][N:5]2[CH2:26][CH2:25][C@:12]34[C:13]5[C:14]6[O:24][C@H:11]3[C@H:10]([N:27]3[C:31](=[O:32])[C:30]7=[C:33]([O:37][CH3:40])[CH:34]=[CH:35][CH:36]=[C:29]7[C:28]3=[O:38])[CH2:9][CH2:8][C@@:7]4([OH:39])[C@H:6]2[CH2:19][C:18]=5[CH:17]=[CH:16][C:15]=6[O:20][CH2:21][O:22][CH3:23])[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 69300357HCID 69300357, compound

Product 1

HCID 69300194HCID 69300194, compoundYield 93.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 5 mL of DMF, 119 mg (0.22 mmol) of N-(17-cyclopropylmethyl-4,5α-epoxy-14-hydroxy-3-methoxymethoxy-morphinan-6-yl)-3-hydroxy-phthalimide obtained in Example 102-1 was dissolved, and 93 mg of potassium carbonate and 0.02 mL of methyl iodide were added thereto, followed by stirring the mixture at room temperature for 3.5 hours. Aqueous saturated sodium hydrogen carbonate solution was added to this reaction solution, and the resulting mixture was extracted with chloroform. Organic layers were combined, washed with saturated saline, dried over anhydrous magnesium sulfate and concentrated to obtain 112 mg of N-(17-cyclopropylmethyl-4,5α-epoxy-14-hydroxy-3-methoxymethoxy-morphinan-6β-yl)-3-methoxy-phthalimide as a crude product.

Workup

  1. extractionthe resulting mixture was extracted with chloroform
  2. washwashed with saturated saline
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-4130817f3ac541a1853070f1cfed20fe
Source dataset
uspto-grants-2008_01
Patent number
US07320984B2

Reaction notes

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