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

HRID 1435893ノート

反応式

HRID 1435893 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
100 °C

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-deef35772eb84e4291fd71625942ff20
出典データセット
uspto-grants-2009_11
特許番号
US07618979B2

反応ノート

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