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

HRID 1937726

반응식

HRID 1937726 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

(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 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 (1,5L) 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).

후처리

  1. customAfter the exothermic 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 (1,5L)
  9. additiontoluene-p-sulphonic acid (0.5 g) was added
  10. temperatureThe mixture was heated
  11. temperatureunder reflux overnight
  12. customcrystallised

출처 및 근거

ORD 기록
ord-567d0f352f694ca785f48c23cb95f136
출처 데이터셋
uspto-grants-2002_05
특허 번호
US06395902B1

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