反応 #60508

反応方程式

Lithium aluminum hydride

2-{4-[2-(3,3,5,5-tetramethylcyclohexyl)phenyl]piperazin-1-ylmethyl}cyclopropanecarboxylic acid ethyl ester

Sodium fluoride

water

→

cis-(2-{4-[2-(3,3,5,5-tetramethylcyclohexyl)phenyl]piperazin-1-ylmethyl}cyclopropyl)methanol

trans-(2-{4-[2-(3,3,5,5-tetramethylcyclohexyl)phenyl]piperazin-1-ylmethyl}cyclopropyl)methanol

溶媒

tetrahydrofuran

tetrahydrofuran

反応条件

後処理

1. 1
   workup.STIRRINGby stirring for 1 hour and 30 minutes at room temperature
2. 2
   workup.ADDITIONwas gradually added
3. 3
   workup.STIRRINGAfter stirring for 1 hour
4. 4
   ろ過the insoluble materials were filtered off
5. 5
   濃縮the filtrate was concentrated under reduced pressure
6. 6
   その他The resultant residue was purified by NH silica gel column chromatography (ethyl acetate/heptane)

実験手順

Lithium aluminum hydride (178 mg, 4.68 mmol) was suspended in anhydrous tetrahydrofuran (15 mL), and the suspension was stirred at room temperature under a nitrogen atmosphere. To the suspension was added a solution of 2-{4-[2-(3,3,5,5-tetramethylcyclohexyl)phenyl]piperazin-1-ylmethyl}cyclopropanecarboxylic acid ethyl ester (1 g, 2.34 mmol) produced in Example (91) in anhydrous tetrahydrofuran (15 mL), followed by stirring for 1 hour and 30 minutes at room temperature. Sodium fluoride (1 g) was added to the reaction mixture, and water (0.4 mL) was gradually added while blowing nitrogen. After stirring for 1 hour, the insoluble materials were filtered off and the filtrate was concentrated under reduced pressure. The resultant residue was purified by NH silica gel column chromatography (ethyl acetate/heptane). This procedure gave 173 mg of cis-(2-{4-[2-(3,3,5,5-tetramethylcyclohexyl)phenyl]piperazin-1-ylmethyl}cyclopropyl)methanol as colorless crystals, and 596 mg of trans-(2-{4-[2-(3,3,5,5-tetramethylcyclohexyl)phenyl]piperazin-1-ylmethyl}cyclopropyl)methanol as a colorless oil.

出典