Methyl iodide → Methyl 1-(methyl{[(phenylmethyl)oxy]carbonyl}amino)cyclopropanecarboxylate

HRID 1366570Notes

Reaction equation

[H-].[Na+].[C:3]1([CH2:9][O:10][C:11]([NH:13][C:14]2([C:17]([O:19][CH3:20])=[O:18])[CH2:16][CH2:15]2)=[O:12])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.I[CH3:22]>CN(C=O)C.O>[CH3:22][N:13]([C:11]([O:10][CH2:9][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1)=[O:12])[C:14]1([C:17]([O:19][CH3:20])=[O:18])[CH2:16][CH2:15]1

Participants

Conditions

Temperature: 0 °C

Procedure

Sodium hydride (995 mg, 41.466 mmol) was taken up in DMF (50 mL) and was cooled to 0° C. for 30 min. Then a mixture of methyl 1-({[(phenylmethyl)oxy]carbonyl}amino)cyclopropanecarboxylate (6.46 g, 25.916 mmol) in DMF (25 mL) was slowly added over 10 min. The resulting mixture was allowed to stir for 45 min, and then iodomethane (4.84 mL, 77.74 mmol) was added, and the reaction was allowed to warm to room temperature overnight. The mixture was then carefully diluted with water (10 mL), and the aqueous layer was extracted with Et2O (5×50 mL). The organic extracts were washed with water (5×50 mL), then dried over Na2SO4 and concentrated in vacuo. The crude residue was purified via Combiflash, utilizing a 0%-50 EtOAc/Hex gradient to provide methyl 1-(methyl{[(phenylmethyl)oxy]carbonyl}amino)cyclopropanecarboxylate (16.9 g, >100%) LCMS: (M+H)+: 264.1.

Workup

additionwas slowly added over 10 min
temperatureto warm to room temperature overnight
extractionthe aqueous layer was extracted with Et2O (5×50 mL)
washThe organic extracts were washed with water (5×50 mL)
dry with materialdried over Na2SO4
concentrationconcentrated in vacuo
customThe crude residue was purified via Combiflash

Sources & evidence

ORD record: ord-8a90ab2fb40f4abfb6eeb82784171cf9
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07893056B2

Reaction notes

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