Methyl iodide → HCID 22027369, compound

Temperature

0 °C

Under nitrogen, 4.1 g of the title compound from Step B was added to a suspension of sodium hydride (60% oil suspension) in 30 mL of dry N,N-dimethylformamide, cooled to 0° C. N-(Diphenylmethylene)glycine ethyl ester (4.6 g) was added in portions with no exotherm, and the mixture was stirred at room temperature for 3 hours. Then, 3.4 mL of methyl iodide was added at <30° C. and the reaction mixture was stirred overnight at room temperature. The reaction mixture was diluted with water and extracted with diethyl ether (2×). The combined extracts were washed with saturated brine (1×) and reduced in vacuo to an oil that was then refluxed in 50 mL of 12N HCl for 4 hours. The reaction mixture was reduced in vacuo to an oil, cooled, and slurried with diethyl ether overnight. The ether was then decanted off and the residue was dried in a vacuum oven to give 1.3 g of the desired intermediate as a solid. NMR(CDCl3; 300 MHz): 1.40 and 1.46 (2 doublets, 3H, J is 7.0 Hz), 4.7 (m, 1H), 8.48 (d, 1H, J is 1.8), 8.6 (bs, 3H), 8.79 (d, 1H, J is 1.9 Hz).

1. stirringthe reaction mixture was stirred overnight at room temperature
2. extractionextracted with diethyl ether (2×)
3. washThe combined extracts were washed with saturated brine (1×)
4. temperaturewas then refluxed in 50 mL of 12N HCl for 4 hours
5. temperaturecooled
6. customslurried with diethyl ether overnight
7. customThe ether was then decanted off
8. customthe residue was dried in a vacuum oven

ORD record

ord-6a4dd3eb78ac4e96a9746bc45aadf081

Source dataset

uspto-grants-2006_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07074742B2