Triethylamine → HCID 86714203, compound

HRID 1484206Notes

Reaction equation

HRID 1484206 reaction equation
[CH:1]1([OH:9])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH:3]=[CH:2]1.[CH2:10]([N:17]=[C:18]=[O:19])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(N(CC)CC)C.[Al]>ClCCl>[CH2:10]([NH:17][C:18](=[O:19])[O:9][CH:1]1[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH:3]=[CH:2]1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 8471Triethylamine2×HCID 76639Benzyl isocyanate2×HCID 5359268AluminumHCID 12599566HCID 12599566, compound

Product 1

HCID 86714203HCID 86714203, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (E)-cyclooct-2-enol 31 (minor isomer 100 mg, 0.792 mmol) in dichloromethane (6 mL) were added benzyl isocyanate (101 μL, 110 mg, 0.826 mmol, 1.04 eq) and a drop of triethylamine. The flask was covered with aluminum foil and the solution was stirred under a nitrogen atmosphere at room temperature overnight. Evaporation of the reaction mixture gave mainly starting material. Benzyl isocyanate (200 μL, 220 mg, 1.65 mmol, 2.08 eq) and a drop of triethylamine in dichloromethane (6 mL) were added and the solution was stirred overnight at room temperature, at 50° C. for 1 hr and at 25-30° C. over the weekend. The volatiles were removed by bulb-to-bulb distillation (50° C., 2 hr). The residue was purified by column chromatography to give carbamate 32 (43 mg, 0.166 mmol, 20.9%) as a white solid.

Workup

  1. customEvaporation of the reaction mixture
  2. customgave mainly starting material
  3. stirringthe solution was stirred overnight at room temperature, at 50° C. for 1 hr and at 25-30° C. over the weekend
  4. customThe volatiles were removed by bulb-to-bulb distillation (50° C., 2 hr)
  5. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-5aa85acbde964015868d868b6c5ad9f3
Source dataset
uspto-grants-2016_08
Patent number
US09421274B2

Reaction notes

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