3-(Trifluoromethyl)benzaldehyde → (1R,2S)-2-(3-trifluoromethyl-benzylamino)-cyclopentanecarboxylic acid methyl ester

Temperature

25 °C

(1R,2S)-2-Amino-cyclopentanecarboxylic acid methyl ester hydrochloride (prepared as described in Example 11a, 130 mg, 0.91 mmol) was dissolved in methanol (5 mL). 3-Trifluoromethyl-benzaldehyde (160 mg, 0.91 mmol) was added, stir at 25° C. for 15 min, acetic acid (0.2 mL) added, followed with sodium cyanoborohydride (150 mg, 2.3 mmol) was added and the mixture was stirred at 25° C. for 16 h. The mixture was poured into a mixture of saturated aqueous sodium bicarbonate solution (100 mL) and ethyl acetate (200 mL). The organic layer was washed with saturated aqueous sodium bicarbonate solution (100 mL), saturated aqueous brine solution (100 mL), dried over magnesium sulfate, filtered, and concentrated in vacuo to afford the crude product (1R,2S)-2-(3-trifluoromethyl-benzylamino)-cyclopentanecarboxylic acid methyl ester (200 mg, 0.664 mmol, 73%), as a clear oil. LC-MS (ESI) calcd for C15H18F3NO2 301.13, found 302.2 [M+H+].

1. additionwas added
2. stirringthe mixture was stirred at 25° C. for 16 h
3. washThe organic layer was washed with saturated aqueous sodium bicarbonate solution (100 mL), saturated aqueous brine solution (100 mL)
4. dry with materialdried over magnesium sulfate
5. filtrationfiltered
6. concentrationconcentrated in vacuo

ORD record

ord-41d71ff2bdcc4a8f8f9c0f9f6e4911d8

Source dataset

uspto-grants-2009_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07582626B2