Ethylamine → HCID 57671198, compound

Temperature

50 °C

A solution of 2-oxo-cyclopentanecarboxylic acid ethyl ester (3.00 g, 19.2 mmol) in ethanol (20 mL) was treated with a 2.0 M solution of ethylamine in tetrahydrofuran (9.6 mL, 19.2 mmol), sodium cyanoborohydride (2.42 g, 38.4 mmol), and glacial acetic acid (10 drops) and stirred for 16 h at 50° C. After cooling to 25° C. the solvent was removed in vacuo, the crude material was redissolved in ethyl acetate (100 mL) and washed with saturated aqueous sodium bicarbonate solution (100 mL). The aqueous layer was discarded and the organic layer was washed with 1.0 M aqueous hydrochloric acid solution (50 mL). The organic layer was discarded, 1.0 M aqueous sodium hydroxide solution (75 mL) was added and the aqueous layer was extracted with ethyl acetate (100 mL). The organic layer was dried over sodium sulfate, filtered and the solvent was removed in vacuo to afford the crude product, 2-ethylamino-cyclopent-1-enecarboxylic acid ethyl ester (1.52 g, 8.30 mmol, 43.2%), as a light yellow oil. LC-MS (ESI) calcd for C10H17NO2 183.13, found 184.1 [M+H+].

1. temperatureAfter cooling to 25° C. the solvent
2. customwas removed in vacuo
3. dissolutionthe crude material was redissolved in ethyl acetate (100 mL)
4. washwashed with saturated aqueous sodium bicarbonate solution (100 mL)
5. washthe organic layer was washed with 1.0 M aqueous hydrochloric acid solution (50 mL)
6. addition1.0 M aqueous sodium hydroxide solution (75 mL) was added
7. extractionthe aqueous layer was extracted with ethyl acetate (100 mL)
8. dry with materialThe organic layer was dried over sodium sulfate
9. filtrationfiltered
10. customthe solvent was removed in vacuo

ORD record

ord-f9832d8be73449b7ab7f445b43adc140

Source dataset

uspto-grants-2009_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07582626B2