Tributylphosphine → HCID 22175233, compound

HRID 1797585Notes

Reaction equation

HRID 1797585 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[C:15](=[O:19])[N:14]([CH2:20][CH:21]([CH3:23])[CH3:22])[C:13]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[C:12]2[OH:29])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:30][C:31]([F:37])([F:36])[CH2:32][CH2:33][CH2:34]O.C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>O1CCCC1>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[C:15](=[O:19])[N:14]([CH2:20][CH:21]([CH3:23])[CH3:22])[C:13]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[C:12]2[O:29][CH2:34][CH2:33][CH2:32][C:31]([F:37])([F:36])[F:30])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 1363074,4,4-Trifluorobutan-1-olHCID 54725276HCID 54725276, compound

Product 1

HCID 22175233HCID 22175233, compoundYield 88.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 6-benzyloxy-4-hydroxy-2-isobutyl-1-oxo-1,2-dihydro-3-isoquinolinecarboxylate (5.93 g, 15 mmol), 4,4,4-trifluorobutanol (2.31 g, 18 mmol) and tributylphosphine (7.5 ml, 30 mmol) in tetrahydrofuran (50 mL) was added 1,1′-(azodicarbonyl)dipiperidine (7.57 g, 30 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-benzyloxy-2-isobutyl-1-oxo-4-(4,4,4-trifluorobutoxy)-1,2-dihydro-3-isoquinolinecarboxylate (6.71 g, 88.5%) 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-f91f002366924f0191685b80d2d9ea6a
Source dataset
uspto-grants-2006_04
Patent number
US07034039B2

Reaction notes

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