1-Butanol → HCID 22176009, compound

HRID 1797462Notes

Reaction equation

HRID 1797462 reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([OH:23])=[C:7]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[N:8]([CH2:13][C:14]([CH3:17])([CH3:16])[CH3:15])[C:9]2=[O:12])=[CH:4][CH:3]=1.[CH2:24](O)[CH2:25][CH2:26][CH3:27].C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>O1CCCC1>[CH2:24]([O:23][C:6]1[C:5]2[C:10](=[CH:11][C:2]([F:1])=[CH:3][CH:4]=2)[C:9](=[O:12])[N:8]([CH2:13][C:14]([CH3:17])([CH3:16])[CH3:15])[C:7]=1[C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:25][CH2:26][CH3:27]

Participants

6

Reactant 4

HCID 2631-ButanolHCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 54725311HCID 54725311, compound

Product 1

HCID 22176009HCID 22176009, compoundYield 94.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 7-fluoro-4-hydroxy-2-neopentyl-1-oxo-1,2-dihydro-3-isoquinolinecarboxylate (5.12 g, 31.9%) (from Example 1(1), 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′-(azodicarbonyl)dipiperidine (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-7-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-2217fe369fb14b60b3aef4e8e949f2ac
Source dataset
uspto-grants-2006_04
Patent number
US07034039B2

Reaction notes

Loading…