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

HRID 368696

反応式

HRID 368696 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

HCID 21339422(R)-N-(2-pyridyl)-2-aminopropanol収率 87.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

(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).

後処理

  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

出典と根拠

ORDレコード
ord-aecfbfc743344929a9c049f7be52c6d3
出典データセット
uspto-grants-2000_10
特許番号
US06133449

関連ノート

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