Trimethylsilyl iodide → (S)-1-(5-Fluoropyridin-2-yl)ethanamine

Participants

Reaction Steps

(1R,2S,5R)-2-Isopropyl-5-methylcyclohexyl [(1S)-1-(5-fluoropyridin-2-ypethyl]carbamate (Method 5; 3.0 g, 9.3 mmol) and TMSI (2.7 ml, 18.6 mmol) in chloroform (10 ml) was heated at 68° C. for 24 hours. Ice water (15 ml) was added carefully and extracted with ether (2×100 ml). The aqueous layer was separated, neutralized with solid sodium bicarbonate to PH=9 and extracted with ether (5×200 ml). The combined organic was dried over sodium sulfate and concentrated to give the title compound (1.03 g, 79%) as pale yellow oil. 1H NMR (400 MHz) 8.44 (d, J=2.8 Hz, 1H), 7.66 (ddd, J=2.8, 2.8 and 2.8 Hz, 1H), 7.53 (m, 1H), 4.01 (q, J=6.8 Hz, 1H), 1.94 (b, 2H), 1.26 (d, J=6.8 Hz, 3H). MS: Calcd.: 140. Found: [M+H]+141.

Provenance & Evidence