1-Butanol → HCID 22176065, compound

HRID 1797457Notes

Reaction equation

HRID 1797457 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[N:7]([CH2:13][C:14]([CH3:17])([CH3:16])[CH3:15])[C:6]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:5]2[OH:23].[CH2:24](O)[CH2:25][CH2:26][CH3:27].C(P(CCCC)CCCC)CCC>O1CCCC1>[CH2:24]([O:23][C:5]1[C:4]2[C:9](=[CH:10][CH:11]=[C:2]([F:1])[CH:3]=2)[C:8](=[O:12])[N:7]([CH2:13][C:14]([CH3:17])([CH3:15])[CH3:16])[C:6]=1[C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:25][CH2:26][CH3:27]

Participants

5

Reactant 3

HCID 2631-ButanolHCID 13831TributylphosphineHCID 54725313HCID 54725313, compound

Product 1

HCID 22176065HCID 22176065, compoundYield 94.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 6-fluoro-4-hydroxy-2-neopentyl-1-oxo-1,2-dihydro-3-isoquinolinecarboxylate (3.21 g, 10 mmol), 1-butanol (1.4 ml, 15 mmol) and tributylphosphine (5.0 ml, 20 mmol) in tetrahydrofuran (30 ml) was added 1,1′-azodicarbonylpiperidine (5.05 g, 20 mmol) and the mixture was stirred at room temperature for 3 h. The reaction mixture was concentrated under reduced pressure and the residue was purified by silica gel column chromatography to give ethyl 4-butoxy-6-fluoro-2-neopentyl-1-oxo-1,2-dihydro-3-isoquinolinecarboxylate (3.55 g, 94.2%) as an oil.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-d78178731e4a4d63a56ef190c9a47c74
Source dataset
uspto-grants-2006_04
Patent number
US07034039B2

Reaction notes

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