Methanesulfonic Acid → Methanesulfonic Acid

Participants

Reaction Steps

Step E comprises reduction of the amide carbonyl of compound VI by slowly adding a Lewis acid such as boron trifluoride etherate or aluminum chloride or an anhydrous strong acid such as methanesulfonic acid or trifluoroacetic acid to a stirred slurry of VI and sodium borohydride in dry THF at about -5° C. to about +5° C. followed by stirring about 4 to 6 hours at about -5° to +5° C. followed by 12 to 18 hours at about 25°-40° C. On completion, the reaction mixture is slowly added to cooled dilute acid followed by isolation by standard procedures if desired. As one skilled in the art would appreciate, the above reaction with sodium borohydride in dry THF and an acid such as boron trifluoride etherate or methanesulfonic acid produces borane-tetrahydrofuran in the process of forming compound VII. Alternatively, compound VII can be formed by reducing compound VI with borane-tetrahydrofuran or borane-dimethyl sulfide, without use of the acid.

Provenance & Evidence