Methanol → N-carbobenzoxy-L-leucinal

Participants

Reaction Steps

A solution of (S)--N--(benzyloxycarbonyl)leucine methyl ester (8.22 g, 29.4 mmol) in dry toluene (80 ml) was treated dropwise at -78° C. with a solution of di-iso-butylaluminium hydride (1.0 M, 74 ml, 74 mmol) in toluene. The solution was stirred at -78° C. for 30 min. before methanol (3.5 ml) was added to quench the reaction. The cold mixture was then added to a stirred aqueous solution of potassium hydrogen tartrate (200 ml). After further stirring for 1 hour the mixture was extracted with ether (3×200 ml), the combined extracts washed with brine (400 ml), dried (MgSO4) and evaporated in vacuo to provide the title compound as a colourless oil. This material was used without purification in the next step.

Provenance & Evidence