Methyl Acrylate → methyl 1-chloro-8-oxo-7,8-dihydro-6H-pyrido[3,4-b]pyrrolizine-7-carboxylate

HRID 1435893노트

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HRID 1435893 반응식
[Cl:1][C:2]1[C:7]2[CH:8]=[C:9]([C:11]([O:13]C)=O)[NH:10][C:6]=2[CH:5]=[CH:4][N:3]=1.CC(C)([O-])C.[K+].[C:21]([O:25][CH3:26])(=[O:24])[CH:22]=[CH2:23].[NH4+].[Cl-]>C1COCC1.C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:7]2[CH:8]=[C:9]3[N:10]([C:6]=2[CH:5]=[CH:4][N:3]=1)[CH2:23][CH:22]([C:21]([O:25][CH3:26])=[O:24])[C:11]3=[O:13]

참가 물질

7

반응물 4

HCID 7294Methyl AcrylateHCID 25517Ammonium ChlorideHCID 23665647Potassium tert-butoxideHCID 26599236methyl 4-chloro-1H-pyrrolo[3,2-c]pyridine-2-carboxylate

생성물 1

HCID 77230298methyl 1-chloro-8-oxo-7,8-dihydro-6H-pyrido[3,4-b]pyrrolizine-7-carboxylate

시약·촉매·용매 2

HCID 1140Toluene용매HCID 8028Tetrahydrofuran용매

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온도
100 °C

실험 절차

To a suspension of methyl 4-chloro-1H-pyrrolo[3,2-c]pyridine-2-carboxylate (12.5 g, 59 mmol) in THF (116 mL)-toluene (460 mL) were added a 1.0 M TBF solution of potassium tert-butoxide (64 mL, 64 mmol) and methyl acrylate (55 mL, 611 mmol). The resulting mixture was heated at 100° C. for 18 h. After this time, the suspension was cooled to room temperature and it was poured into a mixture of saturated aqueous NH4Cl (400 mL) and hexanes (400 mL). The solids were decanted, filtered and washed with H2O and hexanes to provide the title compound.

후처리

  1. temperatureAfter this time, the suspension was cooled to room temperature
  2. customThe solids were decanted
  3. filtrationfiltered
  4. washwashed with H2O and hexanes

출처 및 근거

ORD 기록
ord-deef35772eb84e4291fd71625942ff20
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07618979B2

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