Water → HCID 67537087, compound

HRID 2383061Notes

Reaction equation

HRID 2383061 reaction equation
[CH:1]1([CH:7]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([OH:17])[CH:15]=3)[CH2:10][CH2:9][N:8]2[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl[CH2:26][C:27]([CH3:29])=[O:28].C(=O)([O-])[O-].[K+].[K+].O>C(#N)C.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH:1]1([CH:7]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([O:17][CH2:26][C:27](=[O:28])[CH3:29])[CH:15]=3)[CH2:10][CH2:9][N:8]2[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

7

Reactant 4

HCID 962WaterHCID 6571ChloroacetoneHCID 11430Potassium CarbonateHCID 67536762HCID 67536762, compound

Product 1

HCID 67537087HCID 67537087, compound

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

Tert-butyl 1-cyclohexyl-7-hydroxy-3,4-dihydroisoquinoline-2(1H)-carboxylate (700 mg) was dissolved in acetonitrile (12 mL). 1-chloroacetone (0.2 mL), potassium carbonate (438 mg), and tetra-n-butylammonium iodide (78 mg) were added thereto, followed by stirring at 60° C. for 16 hours. Then, water was added to the mixture which was then extracted with EtOAc. The extract was washed with saturated brine, and then dried over magnesium sulfate. The solvent was evaporated and the resulting residue was purified by silica gel column chromatography (hexane-EtOAc) to obtain tert-butyl 1-cyclohexyl-7-(2-oxopropoxy)-3,4-dihydroisoquinoline-2(1H)-carboxylate (818 mg).

Workup

  1. extractionwas then extracted with EtOAc
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was evaporated
  5. customthe resulting residue was purified by silica gel column chromatography (hexane-EtOAc)

Sources & evidence

ORD record
ord-68eb8ec03e4a41ea9dd86424312b2b25
Source dataset
uspto-grants-2012_09
Patent number
US08263607B2

Reaction notes

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