2-Bromoethyl methyl ether → Methyl 2-(2-methoxyethyl)tricyclo[3.3.1.13,7]decane-2-carboxylate

HRID 588680Notes

Reaction equation

HRID 588680 reaction equation
[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH:2]1[C:11]([O:13][CH3:14])=[O:12])[CH2:8]2.C([N-]C(C)C)(C)C.[Li+].[CH3:23][O:24][CH2:25][CH2:26]Br>O1CCCC1>[CH3:23][O:24][CH2:25][CH2:26][C:2]1([C:11]([O:13][CH3:14])=[O:12])[CH:1]2[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]1[CH2:4]3)[CH2:8]2

Participants

5

Reactant 3

HCID 809722-Bromoethyl methyl etherHCID 2724682Lithium diisopropylamideHCID 12600018Methyl tricyclo[3.3.1.13,7]decane-2-carboxylate

Product 1

HCID 89498778Methyl 2-(2-methoxyethyl)tricyclo[3.3.1.13,7]decane-2-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of EXAMPLE 56A (0.314 g) in tetrahydrofuran (5 mL) was added dropwise lithium diisopropylamide (1.401 mL) at −78° C. The reaction mixture was stirred for 60 minutes and 2-bromoethyl methyl ether (0.562 g) was added. The reaction mixture was slowly warmed up to room temperature, stirred at room temperature overnight, quenched with saturated aqueous NH4Cl solution (2 mL), and extracted with ether. The combined organic layer was dried over Na2SO4, filtered, concentrated and purified by flash chromotography (silica 40 g, 0%-30% ethyl acetate/hexanes).

Workup

  1. stirringstirred at room temperature overnight
  2. customquenched with saturated aqueous NH4Cl solution (2 mL)
  3. extractionextracted with ether
  4. dry with materialThe combined organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by flash chromotography (silica 40 g, 0%-30% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-635b0f160004413da94a3baf183a77fc
Source dataset
uspto-grants-2016_01
Patent number
US09227963B2

Reaction notes

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