Methyl iodide → HCID 86648183, compound

HRID 707048Notes

Reaction equation

HRID 707048 reaction equation
[C:1]([O:5][C:6](=[O:17])[NH:7][CH2:8][CH:9]1[CH2:14][CH2:13][CH:12]([C:15]#[N:16])[CH2:11][CH2:10]1)([CH3:4])([CH3:3])[CH3:2].[CH:18]([N-]C(C)C)(C)C.[Li+].CI>O1CCCC1>[C:1]([O:5][C:6](=[O:17])[NH:7][CH2:8][CH:9]1[CH2:10][CH2:11][C:12]([C:15]#[N:16])([CH3:18])[CH2:13][CH2:14]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 2724682Lithium diisopropylamideHCID 27281767tert-Butyl [(4-cyanocyclohexyl)methyl]carbamate

Product 1

HCID 86648183HCID 86648183, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a cooled (−78° C.) solution of tert-butyl(4-cyanocyclohexyl)methylcarbamate (500 mg) in tetrahydrofuran (10 mL) was added lithium diisopropylamide (2.0 mL, 2M in heptane). The mixture was stirred at −78° C. for 30 minutes before the addition of CH3I (1 mL). The mixture was then stirred and the temperature was allowed to warm to room temperature. The reaction was quenched with aqueous NH4Cl and the mixture was extracted with ethyl acetate (300 mL) and washed with water, brine and dried over Na2SO4. Filtration and evaporation of the solvent and silica gel chromatography (40% ethyl acetate in hexane) of the crude material gave the title compound.

Workup

  1. customThe reaction was quenched with aqueous NH4Cl
  2. extractionthe mixture was extracted with ethyl acetate (300 mL)
  3. washwashed with water, brine
  4. dry with materialdried over Na2SO4
  5. filtrationFiltration and evaporation of the solvent and silica gel chromatography (40% ethyl acetate in hexane) of the crude material

Sources & evidence

ORD record
ord-0a333fc17e414bd8a3cccd32aedb4c93
Source dataset
uspto-grants-2015_11
Patent number
US09174982B2

Reaction notes

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