Sodium Hydroxide → HCID 54541776, compound

Participants

Reaction Steps

25 ml of methanol was cooled to 5° C. and 70 mg (1.8 mmol) of sodium hydroxide and 0.14 g (3.7 mmol) of sodium borohydride were added. To the resulting solution was added dropwise in the range of 5° C. to 10° C. 10 ml of a methanol solution of 2.5 g (13.3 mmol) of the 1-fluoro2-oxo-1-cycloheptanecarboxylic acid methyl ester. After stirring at room temperature for 2 hours, the contents were poured into saturated saline, followed by extraction with ethyl acetate. The extract was successively washed with diluted hydrochloric acid, saline, a saturated sodium bicarbonate solution and saline. The ethyl acetate layer was dried over anhydrous sodium sulfate and the solvent was distilled away to obtain 2.3 g of the crude product. The crude product was purified by silica gel column chromatography (developing solvent: hexane/isopropyl alcohol=99/1) to obtain 1.4 g (yield: 55.4%) of 1-fluoro-2-hydroxycycloheptanecarboxylic acid methyl ester in cis form (compound number 134a; the substance such that the substituent at the 2-position is supposed to take cis configuration when the methoxycarbonyl group at the 1-position is taken as a standard):

Provenance & Evidence