Acetic Acid → 2-Propyl-2,3,4,9-tetrahydro-1H-beta-carboline

HRID 450737

反応式

HRID 450737 の反応式
[CH2:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH2:4][CH2:3][NH:2]1.[CH:14](=O)[CH2:15][CH3:16].C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C1COCC1>[CH2:14]([N:2]1[CH2:3][CH2:4][C:5]2[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[NH:12][C:13]=2[CH2:1]1)[CH2:15][CH3:16]

参加物

6

反応物 4

HCID 176Acetic AcidHCID 527PropanalHCID 107838Tetrahydro-beta-carbolineHCID 5049666Sodium triacetoxyborohydride

生成物 1

HCID 122971032-Propyl-2,3,4,9-tetrahydro-1H-beta-carboline収率 91.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

2,3,4,9-Tetrahydro-1H-beta-carbolin (2.5 g, 14.5 mmol) and propionaldehyde (1.06 ml, 14.5 mmol) were dissolved in THF (100 ml). Acetic acid (1.25 ml, 21.8 mmol) and sodium trisacetoxyborohydride (4.615 g, 21.8 mmol) were sequentially added to the reaction mixture and stirred for 1 h at room temperature. The reaction mixture was concentrated and the residue was dissolved in H2O (10 ml) and ethyl acetate (50 ml). The pH was adjusted to 9 by adding NaOH (2M). The organic phase was separated, dried over magnesium sulfate, filtered, and evaporated to dryness to yield the title product (2.84 g, 91%).

後処理

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionthe residue was dissolved in H2O (10 ml)
  3. additionby adding NaOH (2M)
  4. customThe organic phase was separated
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated to dryness

出典と根拠

ORDレコード
ord-5adf058c61b84e37bdd0a3028761d856
出典データセット
uspto-grants-2013_07
特許番号
US08486984B2

関連ノート

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