Water → HCID 90310884, compound

HRID 927206Notes

Reaction equation

HRID 927206 reaction equation
[CH2:1]([O:8][C:9]1[CH2:13][CH2:12][C:11](=[O:14])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:15]([N-]C(C)C)(C)C.[Li+].CI.O>O1CCCC1.ClCCl>[CH2:1]([O:8][C:9]1[CH2:13][CH:12]([CH3:15])[C:11](=[O:14])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 2724682Lithium diisopropylamideHCID 22756278HCID 22756278, compound2×

Product 1

HCID 90310884HCID 90310884, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-(benzyloxy)cyclopent-2-enone (intermediate 21, 300 mg, 1.59 mmol) in dry tetrahydrofuran (4.0 mL) is cooled at −50° C. with an acetone/dry ice bath and treated with lithium diisopropylamide (2.0 M in tetrahydrofuran, 890 mL, 1.78 mmol). After 15 min methyl iodide (100 μL, 1.59 mmol) is added, and the mixture is warmed to room temperature over night. Water and dichloromethane is added, and the phases are separated. The organic layer is concentrated under reduced pressure, and the residue is purified by reversed phase HPLC (Waters Xbridge™-C18, gradient of acetonitrile in water, 0.1% TFA). Yield: 210 mg; ESI mass spectrum [M+H]+=203; Retention time HPLC: 0.57 min (X012_S01).

Workup

  1. customthe phases are separated
  2. concentrationThe organic layer is concentrated under reduced pressure
  3. customthe residue is purified by reversed phase HPLC (Waters Xbridge™-C18, gradient of acetonitrile in water, 0.1% TFA)
  4. custom0.57 min (X012_S01)

Sources & evidence

ORD record
ord-157d7448de7447cfa519a6129dfe11e0
Source dataset
uspto-grants-2016_03
Patent number
US09290459B1

Reaction notes

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