Methyl iodide → [3-(4-Fluoro-phenyl)-propyl]-methyl-carbamic acid tert-butyl ester

HRID 1158141Notes

Reaction equation

HRID 1158141 reaction equation
[C:1]([O:5][C:6](=[O:18])[NH:7][CH2:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH3:21]I>C1COCC1>[C:1]([O:5][C:6](=[O:18])[N:7]([CH2:8][CH2:9][CH2:10][C:11]1[CH:12]=[CH:13][C:14]([F:17])=[CH:15][CH:16]=1)[CH3:21])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 59512576[3-(4-Fluoro-phenyl)-propyl]-carbamic acid tert-butyl ester

Product 1

HCID 59512610[3-(4-Fluoro-phenyl)-propyl]-methyl-carbamic acid tert-butyl esterYield 101.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of [3-(4-fluoro-phenyl)-propyl]-carbamic acid tert-butyl ester (0.390 g, 1.540 mmol) and NaH (0.092 g, 2.310 mmol, 60% in mineral oil) in 10 mL of THF, was added via a syringe MeI (0.19 mL, 3.080 mmol). After stirring overnight at room temperature under N2, the reaction was quenched with NH4Cl solution (40 mL) and the resulting mixture extracted with dichloromethane (40 mL×3). The combined organic extracts were dried, filtered, and concentrated under reduced pressure. The product was isolated using Flash column chromatography (silica gel) eluting with 0-30% ethyl acetate/hexanes to give the title compound as colorless oil (0.417 g, >99% yield). GC-MS: tR=8.6 min; m/z 267 (M+).

Workup

  1. customthe reaction was quenched with NH4Cl solution (40 mL)
  2. extractionthe resulting mixture extracted with dichloromethane (40 mL×3)
  3. customThe combined organic extracts were dried
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe product was isolated
  7. washeluting with 0-30% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-76957e4e08ed4a0fb0991aebd5dc727a
Source dataset
uspto-grants-2010_10
Patent number
US07807720B2

Reaction notes

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