Sodium Chloride → HCID 89585232, compound

Participants

Reaction Conditions

Reaction Steps

Under a nitrogen atmosphere, 17.2 g (0.058 mol) of tert-butyl (S)-3-(thiazole-2-carbonyl)-piperidine-1-carboxylate were dissolved in 200 ml of tetrahydrofuran, and 121.8 ml (0.122 mol) of lithium tri-tert-butoxyaluminium hydride (1.0 M solution in tetrahydrofuran) were subsequently added dropwise between −4 and +2° C. The reaction mixture was stirred at 0° C. for 30 minutes and then at room temperature for 1 hour. Ice-water was subsequently added, during which the temperature rose to 1° C. After addition of saturated sodium chloride solution and ethyl acetate, the inorganic residue was filtered off. Water and saturated sodium chloride solution were added to the filtrate, which was then extracted with ethyl acetate, and the organic phase was evaporated, giving 19.0 g of tert-butyl (S)-3-(hydroxythiazol-2-ylmethyl)piperidine-1-carboxylate as diastereomer mixture of the S-piperidine in the ratio 30:70 (polar:nonpolar); HPLC/MS (M+H)+=299; rotation value in methanol [α]20D=+4.80. 1H NMR (400 MHz, DMSO) δ 7.72 (dd, J=14.9, 3.3, 1H), 7.62 (dd, J=3.2, 0.8, 1H), 6.22 (dd, J=11.4, 5.3, 1H), 4.66 (dd, J=9.8, 4.6, 1H), 3.82 (t, J=11.8, 2H), 2.71-2.54 (m, 2H), 1.88-1.72 (m, 1H), 1.73-1.57 (m, 2H), 1.40-1.30 (m, 11H).

Provenance & Evidence