Triethylamine → HCID 66744440, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl (3S)-3-hydroxypyrrolidine-1-carboxylate (360 mg, 1.9 mmol) in THF (8 mL) was added triethylamine (253 mg, 349 μL, 2.5 mmol) followed by the addition of CDI (374 mg, 2.3 mmol) portionwise. The reaction mixture was heated at 50° C. for 3 h, cooled to room temperature and diluted with EtOAc. The organic layer was washed with 1 M HCl solution, dried over MgSO4, filtered and concentrated under reduced pressure. The crude material was purified via silica gel column chromatography using 20 to 100% EtOAc in hexanes to obtain (S)-1-(tert-butoxycarbonyl)pyrrolidin-3-yl 1H-imidazole-1-carboxylate (345 mg, 64%). 1HNMR (400 MHz, CDCl3) δ 8.14 (s, 1H), 7.42 (d, J=1.2 Hz, 1H), 7.09 (s, 1H), 4.46 (s, 1H), 3.66 (dd, J=33.8, 10.7 Hz, 1H), 3.56-3.29 (m, 2H), 2.25 (s, 1H), 2.04-1.87 (m, 2H), 1.48 (t, J=4.0 Hz, 9H). LC/MS m/z 282.4 [M+H]+.

Provenance & Evidence