1-Butanol → HCID 22176051, compound

HRID 1797519Notes

Reaction equation

HRID 1797519 reaction equation
[CH:1]1([CH2:4][N:5]2[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:13]([OH:20])[C:12]3[C:7](=[CH:8][CH:9]=[C:10]([F:21])[CH:11]=3)[C:6]2=[O:22])[CH2:3][CH2:2]1.[CH2:23](O)[CH2:24][CH2:25][CH3:26].C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>O1CCCC1>[CH2:23]([O:20][C:13]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([F:21])[CH:11]=2)[C:6](=[O:22])[N:5]([CH2:4][CH:1]2[CH2:3][CH2:2]2)[C:14]=1[C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:24][CH2:25][CH3:26]

Participants

6

Reactant 4

HCID 2631-ButanolHCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 54725283HCID 54725283, compound

Product 1

HCID 22176051HCID 22176051, compoundYield 85.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 2-cyclopropylmethyl-6-fluoro-4-hydroxy-1-oxo-1,2-dihydro-3-isoquinolinecarboxylate (9.16 g, 30 mmol), 1-butanol (3.3 mL, 45 mmol) and tributylphosphine (14.9 mL, 60 mmol) in tetrahydrofuran (100 mL) was added 1,1′-(azodicarbonyl)dipiperidine (15.14 g, 60 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-2-cyclopropylmethyl-6-fluoro-1-oxo-1,2-dihydro-3-isoquinolinecarboxylate (9.24 g, 85.2%) 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-628ae6e69daa4ff49cdae1a3b5d077f5
Source dataset
uspto-grants-2006_04
Patent number
US07034039B2

Reaction notes

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