反応 #69921

反応方程式

4-(2-methoxycarbonylthiophen-3-yl)piperidine-1-carboxylic acid t-butyl ester

MeOH

→

title compound

収率 68.2%

4-(2-Hydroxymethylthiophen-3-yl)piperidine-1-carboxylic Acid t-Butyl Ester

収率 68.2%

溶媒

THF

反応条件

後処理

1. 1
   その他purged with nitrogen (2×)
2. 2
   workup.ADDITIONBorane dimethyl sulfide complex (35 mL, 70 mmol, 110.8 eq.) was added at room temperature
3. 3
   温度the mixture was heated
4. 4
   温度to reflux overnight
5. 5
   濃縮The mixture was then concentrated under vacuum
6. 6
   workup.ADDITIONThe addition of MeOH (20 mL)
7. 7
   濃縮concentrating
8. 8
   その他purified by chromatography with PE/EtOAc (10:1)
9. 9
   その他The product was then purified by preparative HPLC

実験手順

A solution of 4-(2-methoxycarbonylthiophen-3-yl)piperidine-1-carboxylic acid t-butyl ester (2.4 g, 7.4 mmol, 1.0 eq.) in THF (20 mL) was degassed and purged with nitrogen (2×). Borane dimethyl sulfide complex (35 mL, 70 mmol, 110.8 eq.) was added at room temperature and the mixture was heated to reflux overnight. The mixture was allowed to cool to room temperature and MeOH (20 mL) was slowly added. The mixture was then concentrated under vacuum. The addition of MeOH (20 mL) and concentrating was repeated two additional times. The product was applied onto a silica gel column and purified by chromatography with PE/EtOAc (10:1). The product was then purified by preparative HPLC to yield the title compound (1.5 g) as a yellow oil, which gradually solidified.

出典