Diisopropylethylamine → HCID 86714694, compound

HRID 529214Notes

Reaction equation

HRID 529214 reaction equation
C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:12]([O:19][C:20]([CH:22]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH2:25][CH2:24][NH:23]1)=[O:21])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[CH2:32]([O:34][C:35]([C:37]1[O:38][C:39]([CH2:42]Cl)=[CH:40][CH:41]=1)=[O:36])[CH3:33].C(N(CC)C(C)C)(C)C>C(#N)C>[CH2:12]([O:19][C:20]([CH:22]1[CH2:31][C:26]2[C:25](=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:24][N:23]1[CH2:42][C:39]1[O:38][C:37]([C:35]([O:34][CH2:32][CH3:33])=[O:36])=[CH:41][CH:40]=1)=[O:21])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 263166Ethyl 5-(chloromethyl)-2-furancarboxylateHCID 86714695HCID 86714695, compound

Product 1

HCID 86714694HCID 86714694, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 1,2,3,4-tetrahydroisoquinolinecarboxylic acid benzyl ester p-toluenesulfonate (2.1 g, 4.9 mmol) in acetonitrile (15 mL) were added 5-chloromethylfuran-2-carboxylic acid ethyl ester (0.50 mL, 3.3 mmol) and N,N-diisopropylethylamine (1.4 mL, 8.1 mmol), and the mixture was stirred at room temperature for 20 hours. The reaction mixture was concentrated under reduced pressure, and the obtained residue was dissolved in ethyl acetate, and washed successively with saturated aqueous sodium hydrogen carbonate and saturated brine. The organic layer was dried over anhydrous sodium sulfate, and concentrated under reduced pressure and the obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=92/8) to give the title compound (1.1 g, 2.6 mmol, 81%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionthe obtained residue was dissolved in ethyl acetate
  3. washwashed successively with saturated aqueous sodium hydrogen carbonate and saturated brine
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customthe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=92/8)

Sources & evidence

ORD record
ord-fb5fc075bd854f95a438d2382e34247a
Source dataset
uspto-grants-2016_05
Patent number
US09346821B2

Reaction notes

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