Acetic Acid → 8-(1-(cyclopropylmethyl)piperidin-4-yloxy)-3,4-dihydropyrazino[1,2-a]indol-1(2H)-one

HRID 506644노트

반응식

HRID 506644 반응식
[NH:1]1[CH2:6][CH2:5][CH:4]([O:7][C:8]2[CH:16]=[CH:15][C:14]3[N:13]4[CH2:17][CH2:18][NH:19][C:20](=[O:21])[C:12]4=[CH:11][C:10]=3[CH:9]=2)[CH2:3][CH2:2]1.[CH:22]1([CH:25]=O)[CH2:24][CH2:23]1.C(O)(=O)C.C([BH3-])#N.[Na+].C(=O)(O)[O-].[Na+]>O1CCCC1.O>[CH:22]1([CH2:25][N:1]2[CH2:2][CH2:3][CH:4]([O:7][C:8]3[CH:16]=[CH:15][C:14]4[N:13]5[CH2:17][CH2:18][NH:19][C:20](=[O:21])[C:12]5=[CH:11][C:10]=4[CH:9]=3)[CH2:5][CH2:6]2)[CH2:24][CH2:23]1

참가 물질

8

반응물 5

HCID 176Acetic AcidHCID 123114CyclopropanecarboxaldehydeHCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 684610838-(Piperidin-4-yloxy)-3,4-dihydro-2H-pyrazino[1,2-a]indol-1-one

생성물 1

HCID 166795208-(1-(cyclopropylmethyl)piperidin-4-yloxy)-3,4-dihydropyrazino[1,2-a]indol-1(2H)-one수율 30%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
55 °C

실험 절차

To the solution of 0.27 g (0.95 mmol) 8-(piperidin-4-yloxy)-3,4-dihydro-2H-pyrazino[1,2-a]indol-1-one in 6 mL tetrahydrofuran, 20 μL water, 11 μL (99 μg, 1.42 mmol) cyclopropanecarboxaldehyde, 0.16 mL (0.17 g, 2.8 mmol) acetic acid and 1.42 mL (1.42 mmol, 1M solution in tetrahydrofuran) sodium cyanoborohydride were added and the reaction mixture was stirred for 18 hours at 55° C. The mixture was poured on 10% aqueous sodium bicarbonate and was extracted three times with ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered and evaporated. The residue was flash-chromatographed on silica gel with dichloromethane: methanol:ammonia (9:1:0.1 v/v) as eluant to give 96 μg (30%) of the desired compound as a white solid.

후처리

  1. extractionwas extracted three times with ethyl acetate
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was flash-chromatographed on silica gel with dichloromethane: methanol:ammonia (9:1:0.1 v/v) as eluant

출처 및 근거

ORD 기록
ord-1f92fa6bbe804a9c918f00bda966e38f
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07786109B2

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