Sodium hydride → HCID 57937566, compound

Participants

Reaction Conditions

Reaction Steps

1,1-Dimethylethyl 4-hydroxy-1-piperidinecarboxylate (5.50 g, 27.4 mmol) was dissolved in 100.0 mL of THF and cooled to 0° C. Next, sodium hydride (1.19 g, 29.7 mmol, 60% dispersed in mineral oil) was added portion wise and the mixture stirred at rt for 1 h. The mixture was cooled to 0° C. again and 2-chloro-4-fluoropyridine (3.00 g, 22.8 mmol) was added dropwise as a THF solution. The reaction was allowed to stir at rt, and after 6 h TLC indicated that all of the 2-chloro-4-fluoropyridine had reacted. The mixture was again cooled to 0° C. and quenched with water. EtOAc was added and the organics separated. The organics were washed with brine and dried over anhydrous MgSO4, The crude was purified via silica gel chromatography to give 6.14 g (86% yield) of a colorless oil. 1H NMR (400 MHz, DMSO-d6) δ 8.16 (d, J=5.9 Hz, 1H), 7.12 (d, J=2.2 Hz, 1H), 6.99 (d, J=5.9 Hz, 1H), 4.62-4.87 (m, 1H), 3.51-3.69 (m, 2H), 2.96-3.22 (m, 2H), 1.78-1.93 (m, 2H), 1.41-1.57 (m, 2H), 1.36 (s, 9H).

Provenance & Evidence