Carbon Dioxide → HCID 15454918, compound

Participants

Reaction Steps

A suspension of (2S*,3S*,5S*)-1-benzyloxycarbonyl-3-(N-tert-butoxycarbonyl)amino-5-methoxycarbonyl-2-phenylpiperidine (1.01 g, 2.16 mmol) in Hydrogen Chloride, Methanol Reagent 10 (20.0 ml) was stirred and heated at reflux for 10 minutes; the reaction mixture became homogeneous with evolution of CO2 gas. This mixture was concentrated in vacuo, and the syrupy residue was basified with sat. Na2CO3 aq. solution. The mixture was extracted with CH2Cl2 (×4). The combined CH2Cl2 extracts were dried (Na2SO4), and concentrated in vacuo to give crude title compound (0.789 g, quantitative) as a pale yellow syrup. IRmax (film): 3375(m), 3310(w), 1730(br., s), 1700(br., s), 1603(m), 1585(m), 1497(s), 1122(s), 740(s), 700(s) cm-1 ; 1H-NMR δ: 7.45-7.15(m, 10H), 5.26(d, J=5.9 Hz, 1H), 5.15(d, J=12.5 Hz, 1H), 5.01(d, J=12.5 Hz, 1H), 4.51(dd, J=13.9, 2.1 Hz, 1H), 3.65(s, 3H), 3.56-3.43(m, 1H), 3.54(dd, J=13.9, 4.2 Hz, 1H), 2.95-2.85(m, 1H), 2.22(ddd, J=14.9, 4.0, 4.0 Hz, 1H), 1.95(ddd, J=14.9, 10.9, 6.6 Hz, 1H) ppm.

Provenance & Evidence