Water → Methyl 4-oxo-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate

HRID 601794노트

반응식

HRID 601794 반응식
[CH3:1][O:2][C:3]([C:5]1[NH:9][C:8]([CH2:10][CH2:11][C:12]([OH:14])=O)=[CH:7][CH:6]=1)=[O:4].O.C(=O)(O)[O-].[Na+]>ClCCCl>[O:14]=[C:12]1[C:7]2[CH:6]=[C:5]([C:3]([O:2][CH3:1])=[O:4])[NH:9][C:8]=2[CH2:10][CH2:11]1

참가 물질

5

반응물 3

HCID 962WaterHCID 516892Sodium BicarbonateHCID 668739873-[5-(methoxycarbonyl)-1H-pyrrol-2-yl]propanoic acid

생성물 1

HCID 59180145Methyl 4-oxo-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate수율 86.2%

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

반응 조건

온도
100 °C

실험 절차

A suspension of polyphosphoric acid (115%, 109 g) and powdered 3-(5-(methoxycarbonyl)-1H-pyrrol-2-yl)propanoic acid (12.1 g, 51.8 mmol) in 1,2-dichloroethane (40 mL) was heated for 1 h at 100° C. with occasional mixing with a large spatula. Water (100 mL) was added and the mixture was carefully poured into a large Erlenmeyer flask containing solid sodium bicarbonate and ice. The reaction was neutralized (pH 7) and then extracted with EtOAc (5×150 mL). The combined organic extracts were washed with water, NaHCO3, brine, dried (Na2SO4), filtered and concentrated. The crude product was purified by flash chromatography (0-80% EtOAc/Heptane) to afford 8.0 g of methyl 4-oxo-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate (86%). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 2.93-2.98 (m, 2H), 2.99-3.04 (m, 2H), 3.90 (s, 3H), 6.98 (d, J=1.71 Hz, 1H), 9.42 (br s, 1H); LCMS-MS (ESI+) 180.0 (M+H).

후처리

  1. additionwith occasional mixing with a large spatula
  2. additionthe mixture was carefully poured into a large Erlenmeyer flask
  3. extractionextracted with EtOAc (5×150 mL)
  4. washThe combined organic extracts were washed with water, NaHCO3, brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was purified by flash chromatography (0-80% EtOAc/Heptane)

출처 및 근거

ORD 기록
ord-751b7e6f6b444de58a7a8ada4debf1f2
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07902252B2

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