Cyclopentylamine → HCID 69084687, compound

Participants

Reaction Steps

A solution of ((3aR,5R,6S,7R,7aR)-2-(azetidin-1-yl)-6,7-dihydroxy-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazol-5-yl)methyl 4-methylbenzenesulfonate (350 mg, 0.85 mmol) in cyclopentanamine (3 mL) was heated to 50° C. for overnight. The reaction mixture was condensed under vacuum to give a residue, which was purified by Prep-HPLC with the following conditions [(Agilent 1200 prep HPLC): Column, x-Bridge 19*50 mm; mobile phase, Water with 0.05% NH4OH and CH3CN (15% CH3CN up to 28.6% in 5 min Flow rate 20 mL/min; Detector, UV 220 nm)] to give compound 5 as a light yellow solid (30 mg, 11%). (ES, m/z) [M+H]+ 328.0; 1H NMR (300 MHz, DMSO+D2O) 6.25-6.27 (d, J=6.3 Hz, 1H), 3.97 (m, 1H), 3.86 (m, 4H), 3.71 (m, 1H), 3.45 (m, 1H), 3.25 (m, 1H), 2.95 (m, 1H), 2.75 (m, 1H), 2.55 (m, 1H), 2.23 (m, 2H), 1.56-1.72 (m, 6H), 1.25 (m, 2H).

Provenance & Evidence