Water → HCID 86674672, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of (R)-isopropyl 1-(2,3-bis(benzyloxy)propyl)cyclopropane-1-sulfonate (460 g) and KSCN (170 g) in THF 2.2 L) and water (2.2 L) at 25° C. was refluxed for approximately 24 hours at 90° C. until HPLC analysis showed that the reaction had gone to completion. The reaction mixture was concentrated to about 2 L at 40° C. and extracted with MTBE (1.5 L (×3)). The organic layer was discarded and the aqueous layer was neutralized to pH 14 with KOH (30 g) in water (100 mL) and cooled to −5° C. The mixture was neutralized to a pH of between 2 and 3 with concentrated HCl (205 mL) and extracted with ETOAc (2 L (×2)). The combined organic layers was dried over Na2SO4 for approximately 16 hours, filtered and concentrated to dryness to give the product as a deep red oil (265 g).

Provenance & Evidence