Phosphate → HCID 53662183, compound

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Reaction Steps

The cyclopentanone VI (8.6 g.), obtained according to the previous example, is dissolved in 50 ml. of methanol and added to 500 ml. of a phosphate buffer adjusted to a pH of 5.3. Then 20 ml. of an aqueous solution containing an excess of sodium borohydride (1.25 g.) is added at 5° C. After two hours at room temperature, 200 ml. of water is added to the reaction mixture which is then extracted several times with ethyl acetate. The combined organic layers are dried on MgSO4 and then evaporated to dryness giving 8.4 g. (98%) of crude methylester of 5-acetoxy-2-carbomethoxy-3-hydroxycyclopentaneacetic acid. This product examined by gas chromatography exhibits an 80% purity. The product which may be further purified by column chromatography has all the substituent groups with the desired orientation. The compound may not be distilled without decomposition. The principal absorption peaks in the N.M.R. spectrum in CDCl3 occur at the following frequencies expressed in δ units: 2.05 (3H, singlet), 3.65 (3H, singlet), 3.72 (3H, singlet), 4.30-4.70 (1H, multiplet, 5.18-5.43 (1H, multiplet).

Provenance & Evidence