Water → HCID 20634147, compound

HRID 48909Notes

Reaction equation

HRID 48909 reaction equation
[C:1]([C:6]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:7][C:8]1[CH:9]=[C:10]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:11](=[O:18])[N:12]2[C:17]=1[CH:16]=[CH:15][CH:14]=[CH:13]2)([O:3][CH2:4][CH3:5])=[O:2].[BH3-]C#N.[Na+].O>C(O)C>[C:24]([CH:6]([C:1]([O:3][CH2:4][CH3:5])=[O:2])[CH2:7][C:8]1[CH:9]=[C:10]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:11](=[O:18])[N:12]2[C:17]=1[CH:16]=[CH:15][CH:14]=[CH:13]2)([O:26][CH2:27][CH3:28])=[O:25]

Participants

5

Reactant 3

HCID 962WaterHCID 5003444Sodium cyanoborohydrideHCID 20634148HCID 20634148, compound

Product 1

HCID 20634147HCID 20634147, compoundYield 36.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a bright yellow suspension of ethyl 1-(2,2-dicarboethoxyvinyl)-4-oxo-4H-quinolizine-3-carboxylate (12) (750 mg, 1.94 mmol) in 5 ml ethanol was added NaBH3CN (68 mg, 1.08 mmol). The reaction mixture turned red and all solid material dissolved. Stirring was continued for 1 h, and the reaction mixture was poured into 50 ml of water. Ethanol was added to the aqueous suspension until a clear solution was obtained, which was extracted three times with 100 ml dichloromethane. The organic solvent was evaporated and the crude product was purified by flash chromatography to give ethyl 1-(2,2-dicarboethoxyethyl)-4-oxo-4H-quinolizine-3-carboxylate (13) as a bright yellow solid (275 mg, 36%). M.p. 105-108° C. 1H NMR (δ, CDCl3): 1.22 (t, J=7 Hz, 6H), 1.41 (t, J=7 Hz, 3H), 3.41 (d, J=7 Hz, 2H), 3.65 (t, J=7 Hz, 1H), 4.10-4.25 (m, 4H), 4.41 (q, J=7 Hz, 2H), 7.23 (m, 1H), 7.70 (m, 1H), 7.84 (d, J=8 Hz, 1H), 8.33 (s, 1H), 9.50 (d, J=7 Hz, 1H). MS: m/z 389.1466; required for C20H23NO7: 389.1475.

Workup

  1. dissolutionall solid material dissolved
  2. customwas obtained
  3. extractionwhich was extracted three times with 100 ml dichloromethane
  4. customThe organic solvent was evaporated
  5. customthe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-31b3ddc685214e8d9ac035a4fefd2b64
Source dataset
uspto-grants-2004_03
Patent number
US06706528B2

Reaction notes

Loading…