Water → HCID 60064118, compound

HRID 412601Notes

Reaction equation

HRID 412601 reaction equation
[C:1]([N:4]1[CH2:13][CH2:12][C:11]2[C:6](=[CH:7][C:8]([SH:14])=[CH:9][CH:10]=2)[CH2:5]1)(=[O:3])[CH3:2].[H-].[Na+].[C:17]([O:21][C:22]([N:24]1[CH2:29][CH2:28][C:27]([C:33]([O:35][CH2:36][CH3:37])=[O:34])([CH2:30][CH2:31]I)[CH2:26][CH2:25]1)=[O:23])([CH3:20])([CH3:19])[CH3:18].O>CN(C)C=O>[C:17]([O:21][C:22]([N:24]1[CH2:29][CH2:28][C:27]([CH2:30][CH2:31][S:14][C:8]2[CH:7]=[C:6]3[C:11]([CH2:12][CH2:13][N:4]([C:1](=[O:3])[CH3:2])[CH2:5]3)=[CH:10][CH:9]=2)([C:33]([O:35][CH2:36][CH3:37])=[O:34])[CH2:26][CH2:25]1)=[O:23])([CH3:20])([CH3:19])[CH3:18]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 126069591-(3,4-Dihydro-7-mercapto-2(1H)-isoquinolinyl)ethanoneHCID 600641641-(1,1-Dimethylethyl) 4-ethyl 4-(2-iodoethyl)-1,4-piperidinedicarboxylate

Product 1

HCID 60064118HCID 60064118, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

Crude crystals (1.26 g) of 2-acetyl-1,2,3,4-tetrahydroisoquinoline-7-thiol were dissolved in dimethylformamide (15 ml) and thereto were added 60% sodium hydride (243 mg) and 4-ethoxycarbonyl-4-(2-iodoethyl)piperidine-1-carboxylic acid tert-butyl ester (1 g), and the mixture was stirred at 70° C. for 1 hour. After completion of the reaction, water was added and the mixture was extracted with ethyl acetate and washed with saturated brine. The organic layer was dried over anhydrous magnesium sulfate and the solvent was evaporated. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:7) and dried under reduced pressure to give the title compound (535 mg).

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with ethyl acetate
  3. washwashed with saturated brine
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated
  6. customThe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:7)
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-576a0026cdd141b4bfc63f68074159fc
Source dataset
uspto-grants-2003_05
Patent number
US06562828B1

Reaction notes

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