tert-Butyl piperazine-1-carboxylate → HCID 57897237, compound

Participants

Reaction Steps

N-Boc-piperazine (1.42 g, 7.6 mmol, 1.1 eq) was dissolved in 1,2-DCE (20 mL). To this solution, 2-thiazolecarboxaldehyde (0.780 g, 6.91 mmol, 1 eq) in 1,2-DCE (4 mL) was added followed by the portionwise addition of sodium triacetoxyborohydride (2.05 g, 9.68 mmol, 1.4 eq). The mixture was stirred at room temperature for 3 h and then washed with an aqueous saturated solution of NaHCO3. The organic layer was dried (MgSO4), the solvent removed in vacuo and the crude product was purified by column chromatography on a Biotage SP1 system (hexanes/EtOAc; v/v 6:4) to give the title compound (1.95 g, 100%); 1H-NMR (500 MHz, CDCl3): δ 1.47 (s, 9H, C(CH3)3), 2.54 (t, 4H, J=4.7 Hz, piperazine N(CH2)2), 3.48 (t, 4H, J=5.0 Hz, piperazine N(CH2)2), 3.89 (s, 2H, NCH2), 7.30 (d, J=3.5 Hz, 1H, thiazole 5-H), 7.72 (d, J=3.5 Hz, 1H, thiazole 4-H); LC (Method B)-MS (ESI, m/z): Rt=2.84 min—306 [(M+Na)+, 100%].

Provenance & Evidence