Efficient procedures for the large-scale preparation of (1S,2S)-trans-2-methoxycyclohexanol, a key chiral intermediate in the synthesis of tricyclic β-lactam antibiotics

Abstract Enzymatic and chemical resolution methods suitable for preparation of multi-kg quantities of (+)-(1 S ,2 S )-2-methoxycyclohexanol from (+/−) trans -2-methoxycyclohexanol have been developed. The enzymatic resolution was found to offer a particularly simple process affording the resolved product in good yield and excellent enantiomeric excess and has now been operated consistently on a manufacturing scale.