1,2-Dichloroethane → HCID 70026646, compound

Participants

Reaction Steps

To a 13×100 mm threaded vial can be added 4-(3-phenylprop-1-yl)piperidine-TFA salt (0.093 mmol). A solution of 1-(RS)-(N-(methyl)-N-(benzoyl)amino)-3-(SR)-(formyl)-4-(SR)-phenylcyclopentane (19 mg, 0.062 mmol) from Step D (derived from the higher Rf isomer in Step C) and acetic acid (0.006 mL, 0.1 mmol) in 1,2-dichloroethane (1 mL) can then be added to the vial. Sequentially, N,N-diisopropylethylamine (0.022 mL, 0.126 mmol) and a solution of sodium triacetoxyborohydride (26 mg, 0.123 mmol) in 1,2-dichloroethane (2 mL) are then added. The vial is sealed with a septum cap, gently shaken and stored at ambient temperature. After 18 hours, solvent is removed by a stream of warm nitrogen and the residue is redissolved in 80% acetonitrile in water. The sample can be purified on a Gilson Combinatorial Chromatography system using a 9.4 mm×25 cm Zorbax SB-C18 column. Fractions are collected based on the UV absorption and analyzed by mass spec to identify the title compound fractions. These are combined and evaporated.

Provenance & Evidence