Methanol → 11-(3-fluorophenyl)-1-hydroxy-9-methoxy-1,2,3,4-tetrahydro-6H-pyrido[1,2-b]isoquinolin-6-one

HRID 2196377Notes

Reaction equation

HRID 2196377 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]3[CH:16]=[C:15]([O:18][CH3:19])[CH:14]=[CH:13][C:12]=3[C:11](=[O:20])[N:10]3[CH2:21][CH2:22][CH2:23][C:24](=[O:25])[C:9]=23)[CH:5]=[CH:6][CH:7]=1.CO.C(Cl)Cl.[BH4-].[Na+]>CCOC(C)=O>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]3[CH:16]=[C:15]([O:18][CH3:19])[CH:14]=[CH:13][C:12]=3[C:11](=[O:20])[N:10]3[CH2:21][CH2:22][CH2:23][CH:24]([OH:25])[C:9]=23)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 6344DichloromethaneHCID 4311764Sodium borohydrideHCID 1137112611-(3-fluorophenyl)-9-methoxy-3,4-dihydro-2H-pyrido[1,2-b]isoquinoline-1,6-dione

Product 1

HCID 1141649411-(3-fluorophenyl)-1-hydroxy-9-methoxy-1,2,3,4-tetrahydro-6H-pyrido[1,2-b]isoquinolin-6-one

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 11-(3-fluorophenyl)-9-methoxy-3,4-dihydro-2H-pyrido[1,2-b]isoquinoline-1,6-dione in 5 mL 1:1 MeOH:CH2Cl2 was added NaBH4 (17 mg). The reaction was stirred at room temp for 1 h, then diluted with bicarb and EtOAc and stirred for 30 min. The mixture was extracted once with EtOAc, and the organic solution was washed once with brine, dried (Na2SO4) and concentrated. Flash chromtaography (40 g silica, 50-100% EtOAc/hexanes) gave the titled compound.

Workup

  1. stirringstirred for 30 min
  2. extractionThe mixture was extracted once with EtOAc
  3. washthe organic solution was washed once with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-2f88969e3a984030bbe37876f02b1356
Source dataset
uspto-grants-2012_12
Patent number
US08338449B2

Reaction notes

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