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 1715213ノート

反応式

HRID 1715213 の反応式
[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

参加物

5

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-0bbc4b6c72854f979fbe14d484f33a87
出典データセット
uspto-grants-2010_09
特許番号
US07799798B2

反応ノート

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