Potassium Iodide → (R)-1-(2-hydroxyethyl)nipecotic acid ethyl ester

HRID 566563Notes

Reaction equation

HRID 566563 reaction equation
[NH:1]1[CH2:11][CH2:10][CH2:9][CH:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH2:2]1.Br[CH2:13][CH2:14][OH:15].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CC(C)=O>[CH2:7]([O:6][C:4](=[O:5])[C@@H:3]1[CH2:9][CH2:10][CH2:11][N:1]([CH2:13][CH2:14][OH:15])[CH2:2]1)[CH3:8]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 108982-BromoethanolHCID 11430Potassium CarbonateHCID 98969Ethyl nipecotate

Product 1

HCID 54103225(R)-1-(2-hydroxyethyl)nipecotic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

The (R)-enantiomer of ethyl nipecotate (100 g, 0.64 mole) (Akkerman, A. M. et al., Gazz.Chim.Ital., 102 (1972) 189) was mixed in dry acetone (300 ml) with 2-bromoethanol (85 g, 0.68 mole), dried, powdered potassium carbonate (188 g, 1.28 mole) and potassium iodide (21.6 g, 0.13 mole). The reaction mixture was stirred at room temperature for 18 h and at reflux for 24 h. Filtration of the reaction mixture and evaporation of the resultant filtrate gave (R)-1-(2-hydroxyethyl)nipecotic acid ethyl ester as an oil, which was purified by distillation in vacuo (110-115C, 0.1 mmHg), yield (72.2 g, 56%). TLC: rf=0.20 (SiO2; dichloromethane/methanol=19:1).

Workup

  1. customdried
  2. temperatureat reflux for 24 h
  3. filtrationFiltration of the reaction mixture and evaporation of the resultant filtrate

Sources & evidence

ORD record
ord-32b49c956bff439eb40507accc90cb23
Source dataset
uspto-grants-2001_01
Patent number
US06174898B1

Reaction notes

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