Hydrochloric Acid → HCID 68727047, compound

Participants

Reaction Conditions

Reaction Steps

At 5° C., NaBH4 (0.26 g, 6.5 mmol) in methanol (25 ml) was treated with a solution of crude cis-ethyl 7-methyl-9-oxospiro[4.5]decane-6-carboxylate (2.2 g, 9.2 mmol) in methanol (10 ml). The resulting mixture was stirred at 20° C. for 4 h, poured into 2N aqueous HCl (30 ml) and ice/water (50 ml), and extracted twice with MTBE (50 ml). The combined organic phases were washed with water (50 ml), with a saturated aqueous solution of NaCl (50 ml), dried (MgSO4) and concentrated. FC (180 g SiO2, hexane/MTBE 2:1) of the crude product (2.07 g, cis,cis/cis,trans 39:61) gave rel-(6S,7S,9S)-ethyl 9-hydroxy-7-methylspiro[4.5]decane-6-carboxylate (cis,trans; 0.82 g, 37%) and rel-(6S,7S,9R)-ethyl 9-hydroxy-7-methylspiro[4.5]decane-6-carboxylate (cis,cis; 0.49 g, 22%).

Provenance & Evidence