Methyl iodide → HCID 178476334, compound

Participants

Reaction Steps

To an ice-cooled and stirred solution of the crude 26.0 g of trans-acetic acid 4-(2-tert-butoxycarbonylamino-ethyl)-cyclohexylmethyl ester and 5.77 mL (92.6 mmol, 1.1 eq) of CH3I in 300 mL of DMF was added within 15 min 4.04 g (92.58 mmol, 1.1 eq) of NaH (55% in oil). After stirring over night at RT, additional 1.65 mL (26.5 mmol, 0.3 eq) of CH3I and 1.16 g (26.5 mmol, 0.3 eq) of NaH were added and the reaction-mixture was then stirred at RT for 1 h. The compound was then partitioned between ether, 1M HCl solution and water. The organic layer was dried over MgSO4 and concentrated under reduced pressure. The residue was then chromatographed on silica gel with a 4:1 v/v mixture of n-hexane and EtOAc as the eluent giving 18.7 g (68% over 3 steps) of pure trans-acetic acid 4-[2-(tert-butoxycarbonyl-methyl-amino)-ethyl]-cyclohexylmethyl ester as colorless viscous oil, MS: 214 [(M-(tert-butoxycarbonyl))H+].

Provenance & Evidence