Réaction #40778

Équation de réaction

1-Methyl-1,2,5,6-tetrahydro-pyridine-3-carboxylic acid methyl ester

LiAlH4

H2O

NaOH

H2O

→

colorless oil

Rendement 98.9%

(1-Methyl-1,2,5,6-tetrahydro-pyridin-3-yl)-methanol

Rendement 98.9%

Solvants

THF

THF

Conditions de réaction

Traitement

1. 1
   Températurecooled with an ice bath
2. 2
   TempératureThe mixture was cooled with an ice bath
3. 3
   FiltrationThe residue was filtered
4. 4
   Lavagewashed with ether
5. 5
   Concentrationthe filtrate was concentrated in vacuo

Mode opératoire

6.5 g of LiAlH4 (3.2 equiv.) was suspended in 100 mL dry THF and cooled with an ice bath. To this was added dropwise a solution of 8.27 g 1-Methyl-1,2,5,6-tetrahydro-pyridine-3-carboxylic acid methyl ester (free base) in 50 mL dry THF. The mixture was stirred for 3 hours at room temperature. The mixture was cooled with an ice bath and 6.5 mL H2O, 13 mL 2 M NaOH and 6.5 mL H2O were added dropwise. The residue was filtered, washed with ether and the filtrate was concentrated in vacuo to yield 6.7 g of a colorless oil. 1H NMR (400 MHz, CDCl3) δ 2.18-2.26 (m, 2H), 2.36 (s, 3H), 2.49 (t, J=6 Hz, 2H), 2.92-2.97 (m, 2H), 4.00 (br s, 2H), 5.68 (br s, 1H).

Source