Potassium Carbonate → 3-(Indan-5-ylamino)-propionic acid ethyl ester

HRID 12329

反応式

HRID 12329 の反応式
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][CH2:6][CH2:5]2.Cl[CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15].C(=O)([O-])[O-].[K+].[K+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:17]([O:16][C:14](=[O:15])[CH2:13][CH2:12][NH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][CH2:6][CH2:5]2)[CH3:18]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 69341Ethyl 3-chloropropionateHCID 90496Indan-5-amine

生成物 1

HCID 252228753-(Indan-5-ylamino)-propionic acid ethyl ester収率 71%

試薬・触媒・溶媒 1

HCID 74236Tetrabutylammonium Bromide触媒

反応条件

温度
100 °C

実験手順

To a mixture of 5-aminoindane (5 g, 37.6 mmol), ethyl 3-chloropropionate (4.7 mL, 37.6 mmol) and potassium carbonate (5.2 g, 37.6 mmol) was added tetrabutylammonium bromide (200 mg). The mixture was stirred at 100° C. for 16 hours. After cooling to room temperature (rt), the mixture was extracted into ethyl acetate (EtOAc), washed with water, brine and then dried with sodium sulfate (Na2SO4). Removal of the solvent and chromatography on silica, eluting with EtOAc/hexanes (1:20-1:10, v/v), gave 6.2 g (71%) of the title compound. 1H NMR (300 MHz, CDCl3) δ (ppm): 7.03 (d, J=7.6 Hz, 1H), 6.55 (s, 1H), 6.43 (d, J=7.6 Hz, 1H), 4.15 (q, 2H), 3.86 (br, 1H), 3.43 (t, 2H), 2.82 (m, 4H), 2.60 (t, 2H), 2.06 (m, 2H), 1.27 (t, 3H).

後処理

  1. temperatureAfter cooling to room temperature (rt)
  2. extractionthe mixture was extracted into ethyl acetate (EtOAc)
  3. washwashed with water, brine
  4. dry with materialdried with sodium sulfate (Na2SO4)
  5. customRemoval of the solvent and chromatography on silica
  6. washeluting with EtOAc/hexanes (1:20-1:10

出典と根拠

ORDレコード
ord-48ec6b01a3864024ac16587c981afead
出典データセット
uspto-grants-2010_06
特許番号
US07728003B2

関連ノート

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