反应 #959117

反应方程式

5-amino-2-fluoropyridine

4-(4-Formyl-thiazol-2-yl)-piperidine-1-carboxylic acid tert-butyl ester

Sodium triacetoxyborohydride

→

desired product

4-{4-[(6-Fluoro-pyridin-3-ylamino)-methyl]-thiazol-2-yl}-piperidine-1-carboxylic acid tert-butyl ester

溶剂

DCM

反应条件

后处理

1. 1
   洗涤The organic layer was washed with 2M NaOH solution, water, brine
2. 2
   干燥dried (MgSO4)
3. 3
   其他the solvent was removed in vacuo
4. 4
   其他The material was purified by silica gel chromatography (DCM/methanol: 10:1 v/v)

实验过程

5-amino-2-fluoropyridine (0.476 g, 4.2 mmol) was added to 4-(4-Formyl-thiazol-2-yl)-piperidine-1-carboxylic acid tert-butyl ester (0.84 g, 2.8 mmol) in dry DCM (10 mL). Sodium triacetoxyborohydride (0.9 g, 4.2 mmol) was then added. The reaction was stirred for 3 hours at room temperature under N2. The organic layer was washed with 2M NaOH solution, water, brine, dried (MgSO4), and the solvent was removed in vacuo. The material was purified by silica gel chromatography (DCM/methanol: 10:1 v/v) to give the desired product. 1H NMR (CDCl3): δ 7.59-7.60 (1H, m), 7.06-7.10 (1H, m), 7.02 (1H, s), 6.76 (1H, dd, J=8.8, 3.6 Hz), 4.4 (2H, d), 4.20-4.31 (3H, m), 3.09-3.17 (1H, m), 2.8-2.95 (2H, m), 2.07-2.10 (2H, m), 1.77-1.47, (2H, m), 1.47 (9H, s).

来源