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

HRID 450737

반응식

HRID 450737 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-5adf058c61b84e37bdd0a3028761d856
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08486984B2

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