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

HRID 368696

반응식

HRID 368696 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 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).

후처리

  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

출처 및 근거

ORD 기록
ord-aecfbfc743344929a9c049f7be52c6d3
출처 데이터셋
uspto-grants-2000_10
특허 번호
US06133449

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