Water → Methyl (2,2-dimethylpent-4-en-1-yl)carbamate

Temperature

0 °C

A 1 L round-bottom flask under nitrogen was charged with 2,2-Dimethylpent-4-en-1-amine (9.86 g, 87 mmol), diisopropylethylamine (16.73 ml, 96 mmol), and DCM (100 mL) and cooled to 0° C. A solution of methyl chloroformate (7.08 mL, 91 mmol) in DCM (50 mL) was added dropwise. The reaction mixture was warmed to RT, stirred for 24 hours and poured into water. The mixture was extracted with EtOAc (3×). The combined organic portions were washed with brine, dried with anhydrous MgSO4 and filtered, and the solvent was removed from the filtrate by rotary evaporation. The crude product was purified by silica gel chromatography eluting with 70 hexane/30 EtOAc, to give the title compound. 1H NMR (CDCl3): δ 5.85-5.79 (m, 1H), 5.06-5.02 (m, 2H), 4.46 (s, 1H), 3.67 (s, 3H), 3.02-3.00 (m, 2H), 1.98-1.96 (m, 2H), 0.88 (s, 6H) ppm.

1. temperatureThe reaction mixture was warmed to RT
2. extractionThe mixture was extracted with EtOAc (3×)
3. washThe combined organic portions were washed with brine
4. dry with materialdried with anhydrous MgSO4
5. filtrationfiltered
6. customthe solvent was removed from the filtrate by rotary evaporation
7. customThe crude product was purified by silica gel chromatography
8. washeluting with 70 hexane/30 EtOAc

ORD record

ord-9a06fb77b72540698b84e4308fb003e4

Source dataset

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08377874B2