Carbon Dioxide → HCID 59355403, compound

Participants

Reaction Conditions

Reaction Steps

(3-Chloro-pyridin-4-yl)-carbamic acid tert-butyl ester (1.50 g) was dissolved in dry diethyl ether (35 mL), N,N,N′,N′-tertamethylenethylendiamine (2.35 mL) was added and the reaction mixture was cooled in a dry ice/acetone cool bath to −78° C. n-Butyl lithium (9.9 mL, 1.59M in hexane) was added to the suspension, the cool bath was replaced by a sodium chloride/ice mixture and the reaction mixture was stirred at −10° C. for 1.5 h. The suspension was slowly poured on crushed dry ice (2.0 g) in dry diethyl ether (20 mL) and stirred for 1 h. Water was added and the pH was adjusted to −12 by addition of 2N sodium hydroxide solution. The aqueous layer was washed 2× with MTB-ether, 2 M hydrochloric acid was added to the aqueous layer and the pH was adjusted to −2 and the aqueous layer was 3× extracted with ethyl acetate. The combined organic layer was washed with brine, dried over magnesium sulfate and concentrated in vacuum to afford 1.03 g of the title compound of the formula

Provenance & Evidence