1-Butanol → Ethyl 6-bromo-4-butoxy-2-cyclopropylmethyl-1-oxo-1,2-dihydro-3-isoquinolinecarboxylate

HRID 1797504Notes

Reaction equation

HRID 1797504 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[N:7]([CH2:13][CH:14]1[CH2:16][CH2:15]1)[C:6]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[C:5]2[OH:22].[CH2:23](O)[CH2:24][CH2:25][CH3:26].C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>O1CCCC1>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[N:7]([CH2:13][CH:14]1[CH2:15][CH2:16]1)[C:6]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[C:5]2[O:22][CH2:23][CH2:24][CH2:25][CH3:26]

Participants

6

Reactant 4

HCID 2631-ButanolHCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 54725291Ethyl 6-bromo-2-cyclopropylmethyl-4-hydroxy-1-oxo-1,2-dihydro-3-isoquinolinecarboxylate

Product 1

HCID 22176064Ethyl 6-bromo-4-butoxy-2-cyclopropylmethyl-1-oxo-1,2-dihydro-3-isoquinolinecarboxylateYield 85.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 6-bromo-2-cyclopropylmethyl-4-hydroxy-1-oxo-1,2-dihydro-3-isoquinolinecarboxylate (7.32 g, 20 mmol), 1-butanol (2.7 mL, 30 mmol) and tributylphosphine (10.0 mL, 40 mmol) in tetrahydrofuran (100 mL) was added 1,1′-(azodicarbonyl)dipiperidine (10.09 g, 40 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 6-bromo-4-butoxy-2-cyclopropylmethyl-1-oxo-1,2-dihydro-3-isoquinolinecarboxylate (7.24 g, 85.8%) 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-76c5f83eaf304df1af9bcd51bdea0c5d
Source dataset
uspto-grants-2006_04
Patent number
US07034039B2

Reaction notes

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