Water → (+/-)-1-Methyl-3-(6-methyl-2-p-tolyl-imidazo[1,2-a]pyridin-3-yl)-piperidin-2-one

HRID 230259

反応式

HRID 230259 の反応式
CO[C:3](=[O:26])[CH:4]([C:9]1[N:13]2[CH:14]=[C:15]([CH3:18])[CH:16]=[CH:17][C:12]2=[N:11][C:10]=1[C:19]1[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=1)[CH2:5][CH2:6][CH:7]=O.[CH3:27][NH2:28].[BH4-].[Na+].O>CO.CO.CCOC(C)=O>[CH3:27][N:28]1[CH2:7][CH2:6][CH2:5][CH:4]([C:9]2[N:13]3[CH:14]=[C:15]([CH3:18])[CH:16]=[CH:17][C:12]3=[N:11][C:10]=2[C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=2)[C:3]1=[O:26]

参加物

7

反応物 4

HCID 962WaterHCID 6329MethylamineHCID 4311764Sodium borohydrideHCID 587635832-(6-Methyl-2-p-tolyl-imidazo[1,2-a]pyridin-3-yl)-5-oxo-pentanoic acid methyl ester

生成物 1

HCID 11325081(+/-)-1-Methyl-3-(6-methyl-2-p-tolyl-imidazo[1,2-a]pyridin-3-yl)-piperidin-2-one収率 35.6%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 21584119Ethylacetate methanol溶媒

実験手順

To a magnetically stirred solution of (+/−)-2-(6-methyl-2-p-tolyl-imidazo[1,2-a]pyridin-3-yl)-5-oxo-pentanoic acid methyl ester 35c (0.085 g, 0.253 mmol) in methanol (1 mL) at room temperature under Ar atmosphere was added a 40% aqueous solution of methyl amine (MeNH2) (0.021 mL, 0.253 mmol). The reaction mixture was stirred for 1 h at room temperature. NaBH4 (0.019 g, 0.506 mmol) was added at room temperature. After 30 min, water (30 mL) was added, and the aqueous phase was extracted with EtOAc (2×50 mL). The combined organic layers were dried (MgSO4), and concentrated in vacuo to the crude product. The pure product was obtained by column chromatography over silica gel (EtOAc, then 4:96 MeOH/EtOAc as eluent) which gave the title compound (0.03 g, 31%) as a white solid. The combined organic layers were washed with water, dried (MgSO4), and concentrated in vacuo to the crude product. 1H NMR (400 MHz, CDCl3) δ 1.99 (m, 3H), 2.11 (m, 1H), 2.31 (s, 3H), 2.38 (s, 3H), 3.05 (s, 3H), 3.41 (m, 1H), 3.53 (m, 1H), 4.25 (m, 1H), 6.99 (d, J=9.1 Hz, 1H), 7.22 (m, 3H), 7.46 (s, 1H), 7.53 (m, 2H). 13C NMR (100 MHz, CDCl3) δ 18.9, 21.5, 23.1, 26.1, 35.4, 39.7, 50.3, 117.4, 119.1, 121.5, 121.7, 127.0, 129.1, 129.3, 132.4, 137.5, 143.9, 144.4, 168.7. Mass spectrum m/e 335 (M+).

後処理

  1. waitAfter 30 min
  2. extractionthe aqueous phase was extracted with EtOAc (2×50 mL)
  3. dry with materialThe combined organic layers were dried (MgSO4)
  4. concentrationconcentrated in vacuo to the crude product
  5. customThe pure product was obtained by column chromatography over silica gel (EtOAc

出典と根拠

ORDレコード
ord-69a491a78ccc49ef84bbb71870cbf487
出典データセット
uspto-grants-2009_07
特許番号
US07566725B2

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