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

HRID 1937726

反応式

HRID 1937726 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 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).

後処理

  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

出典と根拠

ORDレコード
ord-567d0f352f694ca785f48c23cb95f136
出典データセット
uspto-grants-2002_05
特許番号
US06395902B1

関連ノート

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