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

HRID 1435893Notes

Reaction equation

[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]

Participants

Conditions

Temperature: 100 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-deef35772eb84e4291fd71625942ff20
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07618979B2

Reaction notes

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