Methyl iodide → HCID 69181369, compound

HRID 409668Notes

Reaction equation

HRID 409668 reaction equation
[C:1]([Li])(C)(C)C.[C:6]([O:10][C:11](=[O:23])[NH:12][C:13]1[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[C:15]([O:21][CH3:22])[CH:14]=1)([CH3:9])([CH3:8])[CH3:7].CI.CCOC(C)=O>C1COCC1>[C:6]([O:10][C:11](=[O:23])[NH:12][C:13]1[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[C:15]([O:21][CH3:22])[C:14]=1[CH3:1])([CH3:9])([CH3:8])[CH3:7]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 10634629HCID 10634629, compoundHCID 178418306HCID 178418306, compound

Product 1

HCID 69181369HCID 69181369, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-65 °C

Procedure

A solution of tert-butyllithium (200 mL, 340 mmol, 2.4 equiv, 1.7M in pentane) is added dropwise to a cold (−65° C.) solution of (3,5-dimethoxy-phenyl)-carbamic acid tert-butyl ester (36.1 g, 142 mmol) in THF (250 mL), under an argon atmosphere. The mixture is stirred for min at −65° C. and then allowed to warm to −25° C. A solution of methyliodide (10.7 mL, 171 mmol, 1.2 equiv) in THF (140 mL) is then added. The reaction mixture is allowed to stir for 1 h at −25° C. and then poured onto a mixture of ice/H2O (300 mL) and EtOAc (300 mL). The layers are separated and the aqueous phase is extracted with EtOAc (2×150 mL). The combined organic phase is washed with H2O (3×150 mL) and brine (200 mL), dried (Na2SO4), filtered and concentrated. The residue is purified by silica gel column chromatography (Hex/acetone, 95:5→9:1→4:1) to provide the title compound. ESI-MS: 268.1 [MH]+, TLC: Rf=0.25 (Hex/acetone, 9:1).

Workup

  1. temperatureto warm to −25° C
  2. stirringto stir for 1 h at −25° C.
  3. customThe layers are separated
  4. extractionthe aqueous phase is extracted with EtOAc (2×150 mL)
  5. washThe combined organic phase is washed with H2O (3×150 mL) and brine (200 mL)
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue is purified by silica gel column chromatography (Hex/acetone, 95:5→9:1→4:1)

Sources & evidence

ORD record
ord-f72bc39bd92d4eaf85370399c31ffa4f
Source dataset
uspto-grants-2014_06
Patent number
US08759517B2

Reaction notes

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