Hydrochloric Acid → HCID 89754182, compound

Participants

Reaction Steps

tert-Butyl 4-{[3-(1H-tetrazol-1yl)phenyl]acetyl}piperazine-1-carboxylate (0.80 g, 2.148 mmol) was dissolved in THF (20 ml) and added the borane-tetrahydrofuran complex (4.30 ml, 4.30 mmol) then stirred at RT overnight. TLC showed a less polar spot but still has SM. Added another 2 equiv of borane-THF complex and followed the reaction with TLC. The reaction was first shaken with 1N HCl then basified with 1N NaOH and extracted with ETOAc. The organic layer was dried over Na2SO4, filtered and evaporated to dryness. The residue was chromatographed by MPLC-using 40 g ISCO Redi-sep column and eluted with 50% ethyl acetate/50% hexane to yield t-butyl 4-{2-[3-(1H-tetrazol-1yl)phenyl]ethyl}piperazine-1-carboxylate. LC-MS (IE, m/z): 359 [M+1]+; 1H-NMR (500 MHz, CDCl3) δ ppm 9.04 (s, 1H), 7.64 (s, 1H), 7.60 (t, J=8.2 Hz, 1H), 7.57 (t, J=7.9 Hz, 1H), 7.44 (d, J=7.3 Hz, 1H), 3.87 (b, 4H), 3.32-3.36 (m, 2H), 3.12 (d, J=11.9 Hz, 2H), 3.024-3.06 (m, 2H), 2.70-2.75 (m, 2H), 1.49 (s, 9H);

Provenance & Evidence