Sodium Carbonate → HCID 15454928, compound

Participants

Reaction Steps

To a stirred solution of (2S*,3S*,5S*)-3-amino-1-benzyloxycarbonyl-5-hydroxymethyl-2-phenylpiperidine (0.50 g, 1.36 mmol)) and 2-methoxy-5-trifluoromethoxybenzaldehyde (0.37 g, 1.70 mmol) in CH2Cl2 (20.0 ml) was added NaB(OAc)3H (0.43 g, 2.04 mmol) portionwise. The reaction mixture was stirred at room temperature for 3 hours, and then basified with sat. Na2CO3 aq. solution. The mixture was extracted with CH2Cl2. The combined extracts were dried (Na2SO4), and concentrated in vacuo to give a red oil (0.90 g), which solidified spontaneously on standing in a refrigerator (4 C.). This was flash chromatographed over SiO2 (Merck Kieselgel 60, 18.0 g). Elution with CH2Cl2 --MeOH (300:1/200:1/100:1) gave title compound (0.678 g, 91.6%) as a colorless syrup. IRmax (film): 3450(s), 1698(s), 1682(s), 1670(s), 1498(s), 1230(br., s), 1160(br., s), 1030(s), 738(s), 700(s) cm31 1 ; 1H-NMR δ: 7.44-7.21(m, 9H), 7.18(br.s, 1H), 7.04(br.d, J=8.8 Hz, 1H), 7.00(br.s, 1H), 6.92(d, J=8.8 Hz, 1H), 5.40-5.27(m, 1H), 5.17(d, J=121.5 Hz, 1H), 5.05(d, J=12.5 Hz, 1H), 4.03(br.d, J=13.9 Hz, 1H), 3.74(d, J=13.9 Hz, 1H), 3.70-3.41(m, 4H), 3.62(s, 3H), 3.23-3.11(m, 1H), 2.20-1.95(m, 2H), 1.70-1.45(m, 3H) ppm.

Provenance & Evidence