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

HRID 601794ノート

反応式

HRID 601794 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒

反応条件

温度
100 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-751b7e6f6b444de58a7a8ada4debf1f2
出典データセット
uspto-grants-2011_03
特許番号
US07902252B2

反応ノート

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