Tetrahydrofuran → HCID 86655924, compound

HRID 2060739Notes

Reaction equation

HRID 2060739 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].C1COCC1.[C:24]1([Mg]Br)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[Cl-].[NH4+]>C(Cl)Cl>[OH:2][CH:1]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=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

6

Reactant 4

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 20634151Ethyl 1-formyl-4-oxo-4H-quinolizine-3-carboxylateHCID 178418255HCID 178418255, compound

Product 1

HCID 86655924HCID 86655924, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of ethyl 1-formyl-4-oxo-4H-quinolizine-3-carboxylate (0.400 mg, 1.63 mmol) in 30 mL 1:1 THF:CH2Cl2 at −20° C. was added phenylmagnesium bromide (0.979 mL, 1.96 mmol, 2.0 M in THF) dropwise. The reaction was allowed to warm to rt. After 30 minutes, saturated aqueous ammonium chloride was added, and the mixture was filtered and concentrated to provide crude ethyl 1-[hydroxy(phenyl)methyl]-4-oxo-4H-quinolizine-3-carboxylate as a yellow solid. To a solution of the resultant residue (115 mg, 0.356 mmol) in 4 mL 1:2:1 DMSO:MeOH:H2O was added sodium hydroxide (0.100 g, 2.50 mmoL). The reaction was heated to 60° C. for 1 h, cooled to rt, and subjected to purification via reverse phase HPLC to yield the title compound that gave a mass ion (ES+) of 296.2 for M+H+.

Workup

  1. filtrationthe mixture was filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-3160e8b415204cea8e93bc6a1727900d
Source dataset
uspto-grants-2012_10
Patent number
US08278453B2

Reaction notes

Loading…