Triethylamine → HCID 67233944, compound

Participants

Reaction Conditions

Reaction Steps

(3R,4R)—N-Boc-3-(4-Phenoxybenzenesulfonamido)-4-hydroxy-pyrrolidine (100 mg, 0.23 mmol) was dissolved in trifluoroacetic acid (1 mL) and was stirred until no starting material was detected on TLC (50% ethyl acetate in hexane). The reaction mixture was evaporated under reduced pressure and the residue was dissolved in CH2Cl2 (2 mL). The solution was cooled to 0° C. and triethylamine (71 μL, 0.84 mmol) and Cbz-Cl (41 mg, 0.24 mmol) were added, and the mixture was stirred for 2 hr at room temperature. The solution was washed with water, dried over Na2SO4 and evaporated. The residue was purified by flash chromatography (25% ethyl acetate in hexane) to give (3R,4R)—N-Cbz-3-(4-phenoxybenzenesulfonamido)-4-hydroxypyrrolidine (100 mg, 93%): 1H NMR (300 MHz, CDCl3) δ 7.80 (d, J=9, 2H), 7.42 (t, J=8, 2H), 7.34 (m, 5H), 7.24 (t, J=7, 1H), 7.08 (m, 4H), 5.10 (s, 2H), 4.85 & 4.76 (br s, 1H), 4.34 & 4.26 (br m, 1H), 3.72 (m, 2H), 3.55 (br m, 1H), 3.32 & 3.19 (m, 2H), 2.65 & 2.53 (br s, 1H); [°]20D=−29.5° (c=0.8, CHCl3).

Provenance & Evidence