Ethyl Acetate → Ethyl (2E)-(1-isopropenyl-6,7-dihydro-8H-pyrido[3,4-b]pyrrolizin-8-ylidene)ethanoate

HRID 1435895Notes

Reaction equation

HRID 1435895 reaction equation
[C:1]([C:4]1[C:9]2[CH:10]=[C:11]3[N:15]([C:8]=2[CH:7]=[CH:6][N:5]=1)[CH2:14][CH2:13][C:12]3=O)([CH3:3])=[CH2:2].[H-].[Na+].[NH4+].[Cl-].[CH3:21][CH2:22][O:23][C:24]([CH3:26])=[O:25]>C1COCC1>[C:1]([C:4]1[C:9]2[CH:10]=[C:11]3[N:15]([C:8]=2[CH:7]=[CH:6][N:5]=1)[CH2:14][CH2:13]/[C:12]/3=[CH:26]\[C:24]([O:23][CH2:22][CH3:21])=[O:25])([CH3:3])=[CH2:2]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 57429282HCID 57429282, compound

Product 1

HCID 86601999Ethyl (2E)-(1-isopropenyl-6,7-dihydro-8H-pyrido[3,4-b]pyrrolizin-8-ylidene)ethanoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 1-isopropenyl-6,7-dihydro-8H-pyrido[3,4-b]pyrrolizin-8-one (0.60 g, 2.8 mmol) and triethyl phosphonoacetate (1.00 g, 4.46 mmol) in THF (24 mL) at −78° C. was added 80% NaH (0.12 g, 4.00 mmol), the reaction mixture was allowed to warm to 0° C., then to room temperature. The reaction mixture was poured onto saturated NH4Cl and EtOAc. The organic phase was separated, dried over Na2SO4 and evaporated. The title compound was purified by flash chromatography (40% EtOAc in Hexane).

Workup

  1. customto room temperature
  2. customThe organic phase was separated
  3. dry with materialdried over Na2SO4
  4. customevaporated
  5. customThe title compound was purified by flash chromatography (40% EtOAc in Hexane)

Sources & evidence

ORD record
ord-657bd6725e9c4bb9affd99f7abe10c07
Source dataset
uspto-grants-2009_11
Patent number
US07618979B2

Reaction notes

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