Hydrochloric Acid → 2-Amino-3-(1-fluoro-cyclopentyl)-propionic acid ethyl ester

To a solution of 2-(benzhydrylidene-amino)-3-(1-fluoro-cyclopentyl)-propionic acid ethyl ester (1.36 g, 3.70 mmol) in dichloromethane (10 mL) at 0° C. was added a hydrochloric acid solution (1N, 7.4 mL) and the resulting mixture stirred at room temperature for 17 h. The mixture was separated, the aqueous layer diluted with water (10 mL) and cooled to 0° C. before sodium bicarbonate (1.24 g, 14.8 mmol) was added portionwise. The resulting mixture was extracted with dichloromethane (2×50 mL), the organic phases combined and dried over magnesium sulfate. The mixture was filtered and evaporated which afforded 2-amino-3-(1-fluoro-cyclopentyl)-propionic acid ethyl ester (0.56 g, 75%) as a clear oil: 1H NMR (300 MHz, CDCl3) δ ppm 1.29 (t, J=7.1 Hz, 3H), 1.68 (br. s., 6H), 1.77-1.89 (m, 2H), 1.89-2.15 (m, 3H), 2.15-2.36 (m, 1H), 3.72 (t, J=5.9 Hz, 1H), 4.19 (q, J=7.1 Hz, 2H).

1. customThe mixture was separated
2. additionthe aqueous layer diluted with water (10 mL)
3. additionwas added portionwise
4. extractionThe resulting mixture was extracted with dichloromethane (2×50 mL)
5. dry with materialdried over magnesium sulfate
6. filtrationThe mixture was filtered
7. customevaporated which

ORD record

ord-2c24072e627f48b696c18ccdf525d373

Source dataset

uspto-grants-2010_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07741327B2