Isopropenyl chloroformate → Prop-1-en-2-yl (1-methoxycyclopropane-1-carbonyl)carbamate

A −78° C. solution of 1-methoxycyclopropane-1-carboxamide (0.23 g, 1.998 mmol) in THF (6 mL) was treated drop-wise with lithium bis(trimethylsilyl)amide (1M THF, 2.80 mL, 2.80 mmol), stirred for 0.5 h, treated drop-wise with a solution of isopropenyl chloroformate (0.262 mL, 2.397 mmol) in dry THF (1 mL), stirred for 1 h at −78° C., allowed to slowly warm to RT and stirred for 1 h. The mixture was quenched with satd. NaHCO3), extracted with EtOAc (3×) and the combined organics were dried over Na2SO4 and concentrated to dryness to afford prop-1-en-2-yl (1-methoxycyclopropane-1-carbonyl)carbamate (0.423 g, 106%). MS (ESI) m/z: 222.1 (M+Na+).

1. stirringstirred for 1 h at −78° C.
2. stirringstirred for 1 h
3. customThe mixture was quenched with satd
4. extractionNaHCO3), extracted with EtOAc (3×)
5. dry with materialthe combined organics were dried over Na2SO4
6. concentrationconcentrated to dryness

ORD record

ord-ffa43d0199814058bc12487d20a287be

Source dataset

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09382228B2