Dimethylformamide → HCID 66985235, compound

HRID 1616678Notes

Reaction equation

HRID 1616678 reaction equation
[H-].[Na+].[CH:3]1([C:8]([N:10]2[CH2:17][CH2:16][C@:15]3([CH3:19])[CH2:18][C@@H:11]2[CH2:12][C:13]2[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][C:14]=23)=[O:9])[CH2:7][CH2:6][CH2:5][CH2:4]1.[CH3:25]N(C)C=O.CI>O1CCCC1.O>[CH:3]1([C:8]([N:10]2[CH2:17][CH2:16][C@:15]3([CH3:19])[CH2:18][C@@H:11]2[CH2:12][C:13]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][C:14]=23)=[O:9])[CH2:7][CH2:6][CH2:5][CH2:4]1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 66985202HCID 66985202, compound

Product 1

HCID 66985235HCID 66985235, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (0.01 g) is added to a solution of cyclopentyl-[(2R,6R)-8-hydroxy-6-methyl-1,2,5,6-tetrahydro-4H-2,6-methano-benzo[d]azocin-3-yl]-methanone (0.10 g) in tetrahydrofuran (6 mL; alternatively N,N-dimethylformamide may be used). The mixture is stirred for 30 min at room temperature before methyl iodide (25 μL) is added. The resulting solution is stirred at room temperature overnight. Then, water is added and the resulting mixture is extracted with dichloromethane. The combined extracts are dried (Na2SO4) and the solvent is evaporated. The residue is purified by chromatography on silica gel (cyclohexane/ethyl acetate).

Workup

  1. additionis added
  2. extractionthe resulting mixture is extracted with dichloromethane
  3. dry with materialThe combined extracts are dried (Na2SO4)
  4. customthe solvent is evaporated
  5. customThe residue is purified by chromatography on silica gel (cyclohexane/ethyl acetate)

Sources & evidence

ORD record
ord-909707f991c5481caf77e7dd7be7be07
Source dataset
uspto-grants-2014_07
Patent number
US08765780B2

Reaction notes

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