2-Chloropyridine → (R)-N-(2-pyridyl)-2-aminopropanol

HRID 368696

Reaction equation

HRID 368696 reaction equation
[NH2:1][C@@H:2]([CH2:4][OH:5])[CH3:3].CC(C)([O-])C.[K+].Cl[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1>O1CCCC1>[N:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[NH:1][C@H:2]([CH3:3])[CH2:4][OH:5]

Participants

5

Reactant 3

HCID 79772-ChloropyridineHCID 80308(R)-(-)-2-Amino-1-propanolHCID 23665647Potassium tert-butoxide

Product 1

HCID 21339422(R)-N-(2-pyridyl)-2-aminopropanolYield 87.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(R)-Alaninol (107.3 g, 1.43M) was added dropwise with stirring to a solution of potassium tertiary butoxide (160 g, 1.43M) in tetrahydrofuran (1L). After the exothermic reaction had cooled to room temperature, 2-chloropyridine (162.4 g, 1.43M) was added dropwise. The reaction mixture was heated under reflux overnight, cooled, filtered and evaporated to an oil. The oil was dissolved in xylene (1,5L) and toluene-p-sulphonic acid (0.5 g) was added. The mixture was heated under reflux overnight. On cooling to room temperature the product crystallised to give (R)-N-(2-pyridyl)-2-aminopropanol (190 g), [α]D26 =30° (c=1 in CHCl3).

Workup

  1. customAfter the exothermic reaction
  2. temperatureThe reaction mixture was heated
  3. temperatureunder reflux overnight
  4. temperaturecooled
  5. filtrationfiltered
  6. customevaporated to an oil
  7. dissolutionThe oil was dissolved in xylene (1,5L)
  8. additiontoluene-p-sulphonic acid (0.5 g) was added
  9. temperatureThe mixture was heated
  10. temperatureunder reflux overnight
  11. temperatureOn cooling to room temperature the product
  12. customcrystallised

Sources & evidence

ORD record
ord-aecfbfc743344929a9c049f7be52c6d3
Source dataset
uspto-grants-2000_10
Patent number
US06133449

Linked notes

Loading…