Thiomorpholine 1,1-dioxide → HCID 59756032, compound

Participants

Reaction Conditions

Reaction Steps

(S)-Toluene-4-sulfonic acid 1-benzyl-pyrrolidin-3-yl ester was prepared as described in J. Med. Chem. 1992, 35, 4205. (S)-Toluene-4-sulfonic acid 1-benzyl-pyrrolidin-3-yl ester (400 mg, 1.208 mmol, 1 eq) and 1,1-dioxo-thiomorpholine (817 mg, 6.042 mmol, 5 eq) were taken up in dioxane and heated at 140° C. for 20 hours. The reaction mixture was cooled and the dioxane was removed using rotary evaporation. The resulting residue was purified on a Biotage 40M amine column using a gradient of 0-50% ethyl acetate/hexanes to obtain the title compound (88 mg, 25%) as a yellow oil. 1H NMR (400 MHz) CDCl3 δ 7.30-7.20 (m, 5H), 3.55-3.54 (s, 2H), 3.19-3.17 (m, 1H), 3.01-2.91 (m, 6H), 2.62-2.58 (m, 2H), 2.51-2.43 (m, 2H), 2.00-1.97 (m, 2H), 1.71-1.67 (m, 2H). ESMS m/z: 295.2 [M+H]+.

Provenance & Evidence