Réaction #7306

Équation de réaction

cis-(4-methyl-piperidin-3-yl)-carbamic acid methyl ester

benzaldehyde

sodium triacetoxyborohydride

→

Cis-(1-Benzyl-4-methyl-piperidin-3-yl)-carbamic acid methyl ester

Rendement 70.0%

Solvants

methylene chloride

Conditions de réaction

Traitement

1. 1
   Autreto exotherm to 30°-35° C
2. 2
   AutreThe reaction was quenched with 78 ml saturated sodium bicarbonate (20 volumes)
3. 3
   Extractionextracted into 78 ml methylene chloride (20 volumes)
4. 4
   Concentrationconcentrated to a clear oil

Mode opératoire

The reductive amination of cis-(4-methyl-piperidin-3-yl)-carbamic acid methyl ester was carried out by charging 3.9 grams (1 equiv., 22.6 mmol) to 2.07 ml benzaldehyde (0.9 equiv., 20.4 mmol), 9.6 grams sodium triacetoxyborohydride (2 equivs., 45.3 mmol) and 39 ml methylene chloride (10 volumes). The reaction was stirred at 20° C. and was allowed to exotherm to 30°-35° C. The reaction was complete by GCMS within 30 minutes. The reaction was quenched with 78 ml saturated sodium bicarbonate (20 volumes), extracted into 78 ml methylene chloride (20 volumes) and concentrated to a clear oil. (70% yield). 1H NMR: δ7.2-7.3 (5 H, m, aromatic protons), 5.50-5.48 (1 H, d, J=8.8 Hz), 3.77-3.75 (1 H, d, J=8.0 Hz), 3.63 (3 H, s), 3.45-3.38 (2 H, m), 2.77-2.74 (2 H, d, J=11.2 Hz), 2.14-2.01 (1 H, m), 1.94-1.89 (1 H, m), 1.57-1.55 (1 H, brs), 1.37-1.20 (2 H, m), 0.876 (3 H, d, J=9.2 Hz).

Source