반응 #69921

반응 방정식

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

MeOH

→

title compound

수율 68.2%

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

수율 68.2%

용매

THF

반응 조건

후처리

1. 1
   기타purged with nitrogen (2×)
2. 2
   workup.ADDITIONBorane dimethyl sulfide complex (35 mL, 70 mmol, 110.8 eq.) was added at room temperature
3. 3
   온도the mixture was heated
4. 4
   온도to reflux overnight
5. 5
   농축The mixture was then concentrated under vacuum
6. 6
   workup.ADDITIONThe addition of MeOH (20 mL)
7. 7
   농축concentrating
8. 8
   기타purified by chromatography with PE/EtOAc (10:1)
9. 9
   기타The product was then purified by preparative HPLC

실험 절차

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.

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