Dichloromethane → HCID 86653284, compound

HRID 2389277Notes

Reaction equation

HRID 2389277 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:6](=[O:13])[N:7]2[C:12]=1[CH:11]=[CH:10][CH:9]=[CH:8]2)=[O:2].ClCCl.[BH4-].[Na+]>CO>[OH:2][CH2:1][C:3]1[CH:4]=[C:5]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:6](=[O:13])[N:7]2[C:12]=1[CH:11]=[CH:10][CH:9]=[CH:8]2

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 4311764Sodium borohydrideHCID 20634151Ethyl 1-formyl-4-oxo-4H-quinolizine-3-carboxylate

Product 1

HCID 86653284HCID 86653284, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The ethyl 1-formyl-4-oxo-4H-quinolizine-3-carboxylate (5 g, 20.4 mmol) was stirred in a 2:1 dichloromethane:MeOH solution (102 mL) and cooled to 0° C. The reaction was treated with sodium borohydride (0.309 g, 8.16 mmol), warmed to ambient temperature, and stirred for 20 hours. The mixture was quenched with a 10% sodium carbonate solution, extracted with dichloromethane (3×100 mL), and partitioned between water and dichloromethane. The combined organic extracts were dried over sodium sulfate, filtered and concentrated to afford ethyl 1-(hydroxymethyl)-4-oxo-4H-quinolizine-3-carboxylate.

Workup

  1. customThe mixture was quenched with a 10% sodium carbonate solution
  2. extractionextracted with dichloromethane (3×100 mL)
  3. custompartitioned between water and dichloromethane
  4. dry with materialThe combined organic extracts were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c5f6df44ff1c45dea153ed329fd16e58
Source dataset
uspto-grants-2012_09
Patent number
US08273737B2

Reaction notes

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