Sodium Carbonate → HCID 15454929, compound

Participants

Reaction Steps

To a stirred solution of (2S*,3S*,5R*)-3-amino-1-benzyloxycarbonyl-5-hydroxymethyl-2-phenylpiperidine (0.405 g, 1.14 mmol) and 3-methoxy-5-trifluoromethoxybenzaldehyde (0.301 g, 1.71 mmol) in dry CH2Cl2 (25.0 ml) was added NaB(OAc)3H (0.362 g, 1.71 mmol) portionwise. The mixture was sonicated to dissolve the NaB(OAc)3H added, and then stirred at room temperature for 2 hours and 40 minutes. To this was added sat. Na2CO3 aq. solution (12.0 ml), and the CH2Cl2 layer was separated. The aqueous layer was extracted with CH2Cl2. The combined CH2Cl2 layer and extracts were dried (K2CO3), and concentrated in vacuo to give a pale yellow oil (0.72 g). This was flash chromatographed over SiO2 (Merch Kieselgel 60, 14.0 g). Elution with CH2Cl2 --MeOH (300:1/200:1/100:1) gave title compound [0.416 g, overall 67.0% from (2S*,3S*,5R*)-1-benzyloxycarbonyl-3-(N-tert-butoxy-carbonyl)amino-5-hydroxymethyl-2-phenylpiperidine in two steps] as a colorless syrup. IRmax (film): 3450(s), 1700(s), 1682(s), 1670(s), 1652(s), 1610(w), 1497(s), 1490(s), 1260(br., s), 1220(br., s), 1152(br., s), 1030(s), 738(s), 700(s) cm-1 ; 1H-NMR δ: 7.50-7.11(m, 10H), 7.13-6.93(m, 1H), 6.69(br.d, J=8.4 Hz, 1H), 5.60-5.22(m, 1H), 5.20-4.95(m, 2H), 4.36-4.10(m, 1H), 3.79(d, J=13.9 Hz, 1H), 3.65-3.45(m, 3H), 3.59(br.s, 3H), 3.23-2.95(m, 2H), 2.15(br.s, 1H), 2.02-1.86(m, 1H), 1.86-1.68(m, 1H), 1.68-1.45)m, 2H) ppm.

Provenance & Evidence