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

HRID 12329

반응식

HRID 12329 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 74236Tetrabutylammonium Bromide촉매

반응 조건

온도
100 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-48ec6b01a3864024ac16587c981afead
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07728003B2

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