HCID 87247801, compound → HCID 67046249, compound

HRID 606319Notes

Reaction equation

HRID 606319 reaction equation
[CH2:1]([Mg]Cl)[CH2:2][CH3:3].[CH3:6][O:7][C:8]1[C:9]([CH3:27])=[C:10]([C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:18]([CH:25]=[O:26])=[CH:17][N:16]=2)[C:11]([CH3:14])=[CH:12][CH:13]=1>>[CH3:6][O:7][C:8]1[C:9]([CH3:27])=[C:10]([C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:18]([CH:25]([OH:26])[CH2:1][CH2:2][CH3:3])=[CH:17][N:16]=2)[C:11]([CH3:14])=[CH:12][CH:13]=1

Participants

3

Reactant 2

HCID 87247801HCID 87247801, compoundHCID 178455855HCID 178455855, compound

Product 1

HCID 67046249HCID 67046249, compoundYield 66.6%

Procedure

n-PrMgCl (4.7 ml of 2M solution in THF, 9.36 mmol) is added to a solution of 1-(3-methoxy-2,6-dimethyl-phenyl)-isoquinoline-4-carbaldehyde (2.48 g, 8.51 mmol) dropwise at −78 C and the mixture is allowed to warm to room temperature. After quenching with saturated NH4Cl, the mixture is extracted with EtOAc. The combined extracts are washed with saturated brine, dried over Na2SO4, and concentrated. The residue is chromatographed on silica gel to give 1.9 g of 1-[1-(3-methoxy-2,6-dimethyl-phenyl)-isoquinolin-4-yl]-butan-1-ol as a white foam.

Workup

  1. customAfter quenching with saturated NH4Cl
  2. extractionthe mixture is extracted with EtOAc
  3. washThe combined extracts are washed with saturated brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue is chromatographed on silica gel

Sources & evidence

ORD record
ord-836b164a35464fc68cff3c06693f8968
Source dataset
uspto-grants-2011_03
Patent number
US07915288B2

Reaction notes

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