Dichloromethane → HCID 68817252, compound

Participants

Reaction Steps

(3S,4R)-1-tert-Butyl 3-methyl 4-(benzyl((R)-1-phenylethyl)amino)-3-methylpiperidine-1,3-dicarboxylate (4.777 g, 10.24 mmol) was taken up in 100 mL of 4.4% formic acid in methanol. Palladium on Carbon (10%, 1.059 g) was added and the reaction mixture was stirred under a nitrogen atmosphere for 2 h at room temperature. Filtration through celite gave a colorless solution that was concentrated to give a colorless oil. The oil was combined with 4-(benzyloxy)benzene-1-sulfonyl chloride (4.377 g, 15.48 mmol) and equivalent volumes of CH2Cl2 and saturated sodium bicarbonate, and the resultant biphasic mixture was stirred vigorously overnight. The organic layer was separated and the remaining aqueous phase was washed with CH2Cl2 (3×). the organic extracts were combined, dried over Na2SO4 and concentrated to give a beige solid that was purified by chromatography on silica gel eluting with 30% ethyl acetate/hexanes to give (3S,4R)-1-tert-butyl 3-methyl 4-(4-(benzyloxy)phenylsulfonamido)-3-methylpiperidine-1,3-dicarboxylate as a white solid (4.523 g, 8.72 mmol, 85%). 1H NMR (400 MHz, CHLOROFORM-D) δ ppm 1.14 (s, 3 H) 1.37-1.48 (m, 11H) 1.78 (s, 1H) 2.02-2.05 (m, 3H) 2.51 (s, 1H) 3.08-3.16 (m, 1H) 3.65 (s, 3H) 4.48 (s, 1H) 5.11 (s, 2H) 5.65 (d, J=9.60 Hz, 1H) 7.01-7.06 (m, 2H) 7.31-7.43 (m, 6H) 7.78-7.82 (m, 2H).

Provenance & Evidence