Formaldehyde → 3-(6-hydroxy-1,3-benzodioxol-5-yl)-3-(hydroxymethyl)-1-Pentyl-1,3-dihydro-2H-pyrrolo[3,2-b]pyridin-2-one

HRID 1715213노트

반응식

HRID 1715213 반응식
[OH:1][C:2]1[C:3]([CH:11]2[C:15]3=[N:16][CH:17]=[CH:18][CH:19]=[C:14]3[N:13]([CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[C:12]2=[O:25])=[CH:4][C:5]2[O:9][CH2:8][O:7][C:6]=2[CH:10]=1.C([N-]C(C)C)(C)C.[Li+].[CH2:34]=[O:35]>O1CCCC1>[OH:1][C:2]1[C:3]([C:11]2([CH2:34][OH:35])[C:15]3=[N:16][CH:17]=[CH:18][CH:19]=[C:14]3[N:13]([CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[C:12]2=[O:25])=[CH:4][C:5]2[O:9][CH2:8][O:7][C:6]=2[CH:10]=1

참가 물질

5

반응물 3

HCID 712FormaldehydeHCID 2724682Lithium diisopropylamideHCID 119627753-(6-hydroxy-1,3-benzodioxol-5-yl)-1-pentyl-1,3-dihydro-2H-pyrrolo[3,2-b]pyridin-2-one

생성물 1

HCID 119628133-(6-hydroxy-1,3-benzodioxol-5-yl)-3-(hydroxymethyl)-1-Pentyl-1,3-dihydro-2H-pyrrolo[3,2-b]pyridin-2-one수율 112%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
-78 °C

실험 절차

To a solution of 3-(6-hydroxy-1,3-benzodioxol-5-yl)-1-pentyl-1,3-dihydro-2H-pyrrolo[3,2-b]pyridin-2-one (1.60 g, 4.70 mmol) in anhydrous tetrahydrofuran (30.0 mL) was added a solution of pre-prepared lithium diisopropylamide (10.3 mmol) in anhydrous tetrahydrofuran (30.0 mL) at −78° C. The reaction mixture was stirred at −78° C. for 0.5 h followed by the addiotion of para-formaldehyde (0.85 g, 28.2 mmol) in one portion. The reaction was stirred at −78° C. for 2 h and quenched with saturated ammonium chloride (20.0 mL). After the organic solvent was removed under reduced pressure, the residue was diluted with ethyl acetate (50.0 mL). The organic layer was washed with brine (30.0 mL), dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo to dryness to give the title compound (1.95 g, 100%): 1H NMR (300 MHz, CDCl3) δ 8.22 (dd, 1H), 7.22-7.12 (m, 2H), 6.51 (s, 1H), 6.06 (s, 1H), 5.83 (d, 2H), 4.89 (s, 2H), 3.83-3.61 (m, 2H), 1.75-1.61 (m, 2H), 1.39-1.29 (m, 4H), 0.89 (t, 3H).

후처리

  1. stirringThe reaction was stirred at −78° C. for 2 h
  2. customquenched with saturated ammonium chloride (20.0 mL)
  3. customAfter the organic solvent was removed under reduced pressure
  4. additionthe residue was diluted with ethyl acetate (50.0 mL)
  5. washThe organic layer was washed with brine (30.0 mL)
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated in vacuo to dryness

출처 및 근거

ORD 기록
ord-0bbc4b6c72854f979fbe14d484f33a87
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07799798B2

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