(Diethylamino)sulfur trifluoride → HCID 58674941, compound
Reaction equation
[C:1]([O:5][C:6](=[O:16])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14]O)[N:9]=1)([CH3:4])([CH3:3])[CH3:2].C(N(S(F)(F)[F:23])CC)C>ClCCl>[C:1]([O:5][C:6](=[O:16])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][F:23])[N:9]=1)([CH3:4])([CH3:3])[CH3:2]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of (6-hydroxymethyl-pyridin-2-yl)-carbamic acid tert-butyl ester (prepared as illustrated in example 135) (0.20 g, 0.90 mmol) in dichloromethane (20.00 ml) was cooled under argon to 0° C. and (diethylamino)sulfur trifluoride (DAST) (0.20 g, 1.25 mmol) was added dropwise. The resulting solution was stirred at room temperature for 30 min, then quenched by pouring the reaction mixture onto saturated sodium bicarbonate. The organic phase was separated, dried over sodium sulphate and evaporated to a orange oil, which was purified by flash chromatography (dichloromethane/ether) to yield (6-fluoromethyl-pyridin-2-yl)-carbamic acid tert-butyl ester (0.10 g, 51%) as a colorless oil, MS (ISP): m/e=211.3 (M+H+).