Methyl iodide → HCID 67386001, compound

HRID 905958Notes

Reaction equation

[OH:1][CH2:2][C@H:3]1[CH2:8][CH2:7][CH2:6][C@H:5]([N:9]2[C:17](=[O:18])[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]2=[O:19])[CH2:4]1.[H-].[Na+].I[CH3:23]>CN(C=O)C>[CH3:23][O:1][CH2:2][C@H:3]1[CH2:8][CH2:7][CH2:6][C@H:5]([N:9]2[C:10](=[O:19])[C:11]3[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:17]2=[O:18])[CH2:4]1

Participants

Conditions

Temperature: 0 °C

Procedure

Racemic trans 2-(3-hydroxymethyl-cyclohexyl)-isoindole-1,3-dione (0.37 g, 1.427 mmol) was dissolved in DMF (7 mL) and cooled to 0° C. At that temperature, NaH (60%, 0.136 g, 3.424 mmol) was added, followed by iodomethane (0.54 mL, 8.676 mmol) about 10 minutes later. After another 10 minutes the ice bath was removed, and the reaction mixture was heated to 38° C. After 3 hours, another 6 equivalents of iodomethane were added and the reaction mixture was stirred at 38° C. overnight before being cooled, quenched by addition of saturated aqueous NH4Cl, and extracted times with Et2O. The organic layers were combined, dried (Na2SO4), filtered, and evaporated. The remaining orange oil was purified by SiO2 chromatography (24 g SiO2, hexanes/EtOAc 0 to 10% EtOAc) to give 0.21 g of racemic trans 2-(3-methoxymethyl-cyclohexyl)-isoindole-1,3-dione as white crystalline solid (54% yield).

Workup

customAfter another 10 minutes the ice bath was removed
temperaturethe reaction mixture was heated to 38° C
temperaturebefore being cooled
customquenched by addition of saturated aqueous NH4Cl
extractionextracted times with Et2O
dry with materialdried (Na2SO4)
filtrationfiltered
customevaporated
customThe remaining orange oil was purified by SiO2 chromatography (24 g SiO2, hexanes/EtOAc 0 to 10% EtOAc)

Sources & evidence

ORD record: ord-3be78d9c288f4a0b94071f16f83942db
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08012974B2

Reaction notes

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