Triethylamine → HCID 70983392, compound

HRID 338914Notes

Reaction equation

HRID 338914 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([C:12]3([CH2:15][OH:16])[CH2:14][CH2:13]3)[CH:6]=[CH:7][CH:8]=2)[N:3]=1.C(N(CC)CC)C.[Si:24](OS(C(F)(F)F)(=O)=O)([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[Si:24]([O:16][CH2:15][C:12]1([C:5]2[CH:6]=[CH:7][CH:8]=[C:9]3[C:4]=2[N:3]=[C:2]([CH3:1])[CH:11]=[CH:10]3)[CH2:14][CH2:13]1)([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 516892Sodium BicarbonateHCID 70983047HCID 70983047, compound

Product 1

HCID 70983392HCID 70983392, compoundYield 92.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (1-(2-methylquinolin-8-yl)cyclopropyl)methanol (0.050 g, 0.234 mmol) and triethylamine (0.065 mL, 0.47 mmol) in DCM (5 mL) was added TBSOTf (0.065 mL, 0.28 mmol) at ambient temperature and the reaction was stirred at ambient temperature for 1 hour. Saturated sodium bicarbonate (10 mL) and DCM (20 mL) were added. The organic layer was separated, washed with brine, dried (sodium sulfate), filtered and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (10:1 hexane/ethyl acetate) to give 8-(1-((tert-butyldimethylsilyloxy)methyl)cyclopropyl)-2-methylquinoline (0.071 g, 92.5%) as an oil.

Workup

  1. customThe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried (sodium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash chromatography on silica gel (10:1 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-5d7662d192b54e15a6e0167e80132846
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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