Methyl iodide → HCID 178500382, compound

HRID 2092002Notes

Reaction equation

HRID 2092002 reaction equation
[CH3:1][O:2][C:3](=[O:18])[CH:4]([C@H:6]1[CH2:9][C@H:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:7]1)[CH3:5].[Li+].[CH3:20]C([N-]C(C)C)C.CCCCCC.IC>C1COCC1.O>[CH3:1][O:2][C:3](=[O:18])[C:4]([C@H:6]1[CH2:7][C@H:8]([O:10][CH2:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:9]1)([CH3:20])[CH3:5]

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 8058HexaneHCID 2724682Lithium diisopropylamideHCID 178500469HCID 178500469, compound

Product 1

HCID 178500382HCID 178500382, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a solution of trans-2-(3-benzyloxy-cyclobutyl)-propionic acid methyl ester (94 mg, 0.38 mmol) in THF (1 mL) is added 1.09M LDA in THF and hexane (1.51 mL, 1.65 mmol) at −78° C. under nitrogen, and stirred at −78° C. for 30 minutes. To the mixture, iodomethane (232 uL, 3.76 mmol) is added, and stirred at −78° C. for 30 minutes. The temperature is slowly warmed to room temperature for 3 hours. To the mixture, H2O is added and extracted with AcOEt. The organic layer is dried over MgSO4 and concentrated under reduced pressure to give trans-2-(3-benzyloxy-cyclobutyl)-2-methyl-propionic acid methyl ester (70 mg, 70%); ESI-MS m/z 263 [M+1]+, retention time 2.17 min (condition A).

Workup

  1. stirringstirred at −78° C. for 30 minutes
  2. temperatureThe temperature is slowly warmed to room temperature for 3 hours
  3. extractionextracted with AcOEt
  4. dry with materialThe organic layer is dried over MgSO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f76fbbcc568448588b11afd711400d4a
Source dataset
uspto-grants-2013_05
Patent number
US08440682B2

Reaction notes

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