Water → 1-Methyl-1,2,5,6-tetrahydropyridine-3-methanol

HRID 12500Notes

Reaction equation

HRID 12500 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].C[O:8][C:9]([C:11]1[CH2:12][N:13]([CH3:17])[CH2:14][CH2:15][CH:16]=1)=O.O.[OH-].[Na+]>C1COCC1>[CH3:17][N:13]1[CH2:14][CH2:15][CH:16]=[C:11]([CH2:9][OH:8])[CH2:12]1

Participants

6

Reactant 4

HCID 962Water2×HCID 2230ArecolineHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydride

Product 1

HCID 4247001-Methyl-1,2,5,6-tetrahydropyridine-3-methanolYield 98.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

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).

Workup

  1. temperaturecooled with an ice bath
  2. temperatureThe mixture was cooled with an ice bath
  3. filtrationThe residue was filtered
  4. washwashed with ether
  5. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-2e554649f6b9407aa6af9dc843fd250c
Source dataset
uspto-grants-2010_06
Patent number
US07728018B2

Reaction notes

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