Triethylamine → Ethyl 2-methylaminoindolizine-3-carboxylate

HRID 502475노트

반응식

HRID 502475 반응식
[Br-].[CH2:2]([O:4][C:5]([CH2:7][N+:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:6])[CH3:3].CSC(SC)=C[N+]([O-])=O.[CH3:23][CH2:24][N:25](CC)[CH2:26]C>C(O)C>[CH3:26][NH:25][C:24]1[CH:23]=[C:13]2[N:8]([C:7]=1[C:5]([O:4][CH2:2][CH3:3])=[O:6])[CH:9]=[CH:10][CH:11]=[CH:12]2

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 836231,1-Bis(methylthio)-2-nitroethyleneHCID 87028Pyridinium, 1-(2-ethoxy-2-oxoethyl)-, bromide (1:1)

생성물 1

HCID 12632503Ethyl 2-methylaminoindolizine-3-carboxylate

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A mixture of 1-ethoxycarbonylmethylpyridinium bromide 5 (1 g, 4.1 mmol), 1,1-bismethylthio-2-nitroethene (1.2 g; 8.1 mmol) and Et3N (4.1 g, 40.6 mmol) in ethanol (30 mL) was heated at reflux for 12 h. The solvents and the triethylamine were then evaporated under vacuum. The oil obtained was extracted with water (50 mL) and toluene (3×50 mL). The combined extracts were dried over anhydrous magnesium sulphate, filtered and then concentrated under vacuum. The residue was chromatographed on a column of silica with an elution gradient of 1/1 to 4/1 of ethyl acetate/petroleum ether. This gave 0.5 g of ethyl 2-methylaminoindolizine-3-carboxylate 6 in the form of an oil. 1H NMR (DMSO-d6) δ: 9.11 (br s, 1H), 7.32 (d, J=8.8 Hz, 1H), 7.07-7.01 (m, 1H), 6.71-6.66 (m, 1H), 5.88 (br s, 1H), 5.85 (s, 1H), 4.32 (q, J=7.0 Hz, 2H), 2.85 (d, J=5.1 Hz, 3H), 1.34 (t, J=7.0 Hz, 1H), 13C NMR (CDCl3) δ: 161.0, 148.9, 138.2, 127.0, 123.4, 115.8, 109.9, 98.6, 84.3, 58.7, 31.0, 14.7.

후처리

  1. temperaturewas heated
  2. temperatureat reflux for 12 h
  3. customThe solvents and the triethylamine were then evaporated under vacuum
  4. customThe oil obtained
  5. extractionwas extracted with water (50 mL) and toluene (3×50 mL)
  6. dry with materialThe combined extracts were dried over anhydrous magnesium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum
  9. customThe residue was chromatographed on a column of silica with an elution gradient of 1/1 to 4/1 of ethyl acetate/petroleum ether

출처 및 근거

ORD 기록
ord-4822f2c394654cc28d0b4a10b6eaffc5
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07776107B2

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