tert-Butyl methyl ether → (R)-1-(3-chlorothien-2-yl)-2-butyltoluenesulfonamide lithium salt

Participants

Reaction Conditions

Reaction Steps

Under a nitrogen atmosphere, a solution of 3-chlorothiophene (48.75 g) in TBME (291 g) is cooled to -10° C. and 2.5 M n-butyllithium in hexanes (151.3 mL) is added at such a rate that the reaction temperature is maintained between 0 and 5° C. After the addition is complete, the mixture is cooled to -5° C. and 1-p-toluenesulfonyl-2(R)-ethylaziridine (74.1 g, as a 56.9 % (w/w) solution in TBME) is added at such a rate as to maintain the temperature of the reaction mixture below 9° C. (during which time a solid precipitates). After about 5 minutes, the mixture is cooled to 0° C. and the precipitate is collected by vacuum filtration, washed with 0° C. TBME (60 mL), and dried in vacuo at about 40° C., to give (R)-1-(3-chlorothien-2-yl)-2-butyltoluenesulfonamide lithium salt. m.p. 372° C. (dec.). MS (FAB), m/z 350, 352 (100%), 1HNMR (200 Mhz, DMSO) δ 0.8 (t, 3H): 2.25 (s, 3H); 6.85 (d, 1H); 7.05 (d, 2H), 7.35 (d, 2H).

Provenance & Evidence