Methyl iodide → HCID 19736741, compound

HRID 326316Notes

Reaction equation

[OH:1][C:2]1[CH:16]=[C:15]([O:17][CH2:18][C:19]([O:21]CC)=[O:20])[CH:14]=[C:13]2[C:3]=1[C:4](=[O:24])[CH2:5][C:6]1([NH:12]2)[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1.CI.[C:27](=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:27][O:1][C:2]1[CH:16]=[C:15]([O:17][CH2:18][C:19]([OH:21])=[O:20])[CH:14]=[C:13]2[C:3]=1[C:4](=[O:24])[CH2:5][C:6]1([NH:12]2)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]1

Participants

Conditions

Temperature: 40 °C

Procedure

A mixture of ethyl 2-{(5-hydroxy-4-oxospiro [1,2,3,4-tetrahydroquinoline-2,1'-cyclohexan]-7-yl)oxy}acetate (prepared in Example 51 (1)) (0.15 g, 0.45 mmol), methyl iodide (0.071 g, 0.50 mmol), anhydrous potassium carbonate (0.094 g, 0.68 mmol), and dry DMF (4 ml) is stirred at 40° C. for 9 hours. After the addition of methyl iodide (0.14 g, 1.0 mmol), the stirring is continued for additional 4 hours. The solvent is removed by distillation and the residue is dissolved in ethyl acetate. The solution is washed with saturated brine, dried, and the solvent is removed. The residue is placed on a silica gel column and eluted with a mixture of ethyl acetate and dichloromethane (1:10). The earlier fractions containing oily materials are discarded. From the succeeding fractions, the desired product is obtained as a crystalline solid (0.067 g, 43%, m.p=158°-159° C.).

Workup

waitthe stirring is continued for additional 4 hours
customThe solvent is removed by distillation
dissolutionthe residue is dissolved in ethyl acetate
washThe solution is washed with saturated brine
customdried
customthe solvent is removed
washeluted with a mixture of ethyl acetate and dichloromethane (1:10)
additionThe earlier fractions containing oily materials

Sources & evidence

ORD record: ord-08243adbd9c84bc097d74112255335d5
Source dataset: uspto-grants-1993_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05268386

Reaction notes

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