Triethylamine → HCID 14348565, compound

Participants

Reaction Steps

(2RS,3RS,4SR,5SR)-2-Methyl-3-benzylamino-4-methoxycarbonyl-5-hydroxyhexanoic acid (340 mg; 1.1 mmole) and triphenylphosphine (393 mg; 1.5 mmole) were dissolved in dry toluene (6 ml). After addition of triethylamine (151.5 mg; 1.5 mmole), the resultant mixture was cooled to -15° C. Diethyl azodicarboxylate (261 mg; 1.5 mmole) was added thereto, and the mixture was stirred at -10° to -5° C. for 1 hour. The solvent was removed under reduced pressure, and the residue was purified by silica gel column chromatography to give methyl (2RS,3SR,4RS,5RS)-tetrahydro-2,5-dimethyl6-oxo-4-benzylamino-2H-pyrane-3-c (190 mg) and methyl (2SR,3SR,4RS,5RS)-tetrahydro-2,5-dimethyl-6-oxo-4-benzylamino-2H-pyrane-3-carboxylate (55 mg). (2RS,3SR,4RS,5RS) isomer:

Provenance & Evidence