反応 #53871

反応方程式

LiAlH4

trans-5-[4-(tert-Butoxycarbonyl-methyl-amino)-cyclohexyl]-pent-2-enoic acid ethyl ester

→

trans-[4-(5-Hydroxy pentyl)-cyclohexyl)-methyl-carbamic acid tert-butyl ester

収率 97.0%

溶媒

THF

MeOH

反応条件

後処理

1. 1
   ろ過After filtration and evaporation of the methanol under vacuo, 2.39 g 5-[4-(tert-Butoxy carbonyl-methyl-amino)-cyclohexyl]-pentanoic acid ethyl ester
2. 2
   その他could be isolated
3. 3
   その他Exess of LiAlH4 was destroyed
4. 4
   workup.ADDITIONby adding 10 ml of EtOAc
5. 5
   workup.DISSOLUTIONThe solution was dissolved in ether
6. 6
   洗浄washed with 1N HCl and water
7. 7
   濃縮The organic phase was concentrated under reduced pressure

実験手順

A solution of 2.45 g (7.2 mmol) trans-5-[4-(tert-Butoxycarbonyl-methyl-amino)-cyclohexyl]-pent-2-enoic acid ethyl ester and 200 mg of Pd/C (10%) in 40 ml MeOH was stirred for 20 h under H2-atmosphere. After filtration and evaporation of the methanol under vacuo, 2.39 g 5-[4-(tert-Butoxy carbonyl-methyl-amino)-cyclohexyl]-pentanoic acid ethyl ester could be isolated. 2.05 g (6.0 mmol) of this ester and 470 mg (12 mmol) of LiAlH4 were stirred in 20 ml of THF at RT for 5 h. Exess of LiAlH4 was destroyed by adding 10 ml of EtOAc and by carefully dropping brine to the reaction-mixture. The solution was dissolved in ether and washed with 1N HCl and water. The organic phase was concentrated under reduced pressure yielding 1.75 g (97%) of clean trans-[4-(5-Hydroxy pentyl)-cyclohexyl)-methyl-carbamic acid tert-butyl ester, MS: 300 (MH+).

出典