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

HRID 566586

Reaction equation

HRID 566586 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 (1 L). After the exothernic reaction had cooled to room termperature, 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 (1.5 L) 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 exothernic reaction
  2. additionwas added dropwise
  3. temperatureThe reaction mixture was heated
  4. temperatureunder reflux overnight
  5. temperaturecooled
  6. filtrationfiltered
  7. customevaporated to an oil
  8. dissolutionThe oil was dissolved in xylene (1.5 L)
  9. additiontoluene-p-sulphonic acid (0.5 g) was added
  10. temperatureThe mixture was heated
  11. temperatureunder reflux overnight
  12. customcrystallised

Sources & evidence

ORD record
ord-683561d02eb04facadd8ea712f22925e
Source dataset
uspto-grants-2001_01
Patent number
US06175012B1

Linked notes

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