Iodoethane → (R)-4a-Ethoxymethyl-1-(4-fluorophenyl)-1,4,4a,5,7,8-hexahydro-1,2,6-triazacyclopenta[b]naphthalene-6-carboxylic acid tert-butyl ester

Temperature

50 °C

A solution of (R)-1-(4-fluorophenyl)-4a-hydroxymethyl-1,4,4a,5,7,8-hexahydro-1,2,6-triazacyclopenta[b]naphthalene-6-carboxylic acid tert-butyl ester (0.25 g) in tetrahydrofuran (2.5 mL) under argon at room temperature was treated sequentially with sodium hydride (0.072 g, 60% dispersion in mineral oil) and iodoethane (0.15 mL), and the resulting mixture was stirred at 50° C. for 2 hour. The solution was cooled to room temperature, diluted with ethyl acetate, washed with saturated aqueous ammonium chloride solution, water and brine, and dried over sodium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel, eluting with a mixture of dichloromethane and ethyl acetate (9:1 by volume), to afford the title compound as an amber gum (0.21 g). LCMS (Method E): 428 (M+H)+, Retention time 4.7 minutes.

1. temperatureThe solution was cooled to room temperature
2. washwashed with saturated aqueous ammonium chloride solution, water and brine
3. dry with materialdried over sodium sulfate
4. customThe solvent was removed under reduced pressure
5. customthe residue was purified by column chromatography on silica gel
6. washeluting with a mixture of dichloromethane and ethyl acetate (9:1 by volume)

ORD record

ord-02469d750c2e45fe9445f9b280f73c6c

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08598154B2