Methyl iodide → HCID 178500469, compound

HRID 2092001Notes

Reaction equation

HRID 2092001 reaction equation
[CH3:1][O:2][C:3](=[O:17])[CH2:4][C@H:5]1[CH2:8][C@H:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:6]1.[Li+].[CH3:19]C([N-]C(C)C)C.CCCCCC.IC>C1COCC1.O>[CH3:1][O:2][C:3](=[O:17])[CH:4]([C@H:5]1[CH2:8][C@H:7]([O:9][CH2:10][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:6]1)[CH3:19]

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 8058HexaneHCID 2724682Lithium diisopropylamideHCID 178500717HCID 178500717, compound

Product 1

HCID 178500469HCID 178500469, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a solution of trans-(3-benzyloxy-cyclobutyl)-acetic acid methyl ester (110 mg, 0.47 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 min. To the mixture, iodomethane (232 ul, 3.76 mmol) is added, and the mixture is stirred at −78° C. for 30 min. 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)-propionic acid methyl ester (94 mg, 80%); ESI-MS m/z 249 [M+1]+, retention time 2.07 min (condition A).

Workup

  1. stirringthe mixture is stirred at −78° C. for 30 min
  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-6508e55936ed46f79e3446d010947877
Source dataset
uspto-grants-2013_05
Patent number
US08440682B2

Reaction notes

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