Potassium bisulfate → Tert-butyl N-(1-oxohex-4-YN-2-YL)carbamate

Participants

Reaction Steps

A suspension of lithium aluminum hydride (1.56 g, 41.1 mmol) in ether (150 mL) was stirred at room temperature for 30 minutes. The solution was cooled to -55° C. under nitrogen, and a solution of the product from Step J (11.10 g, 41.1 mmol) in ether (150 mL) was added over 15 min, maintaining the temperature below -50° C. When the addition was complete, the reaction was warmed to 5° C., then recooled to -40° C. A solution of potassium hydrogen sulfate (21.8 g) in 25 mL water was slowly added, maintaining the temperature below -35° C. The mixture was warmed to room temperature and stirred for one hour, filtered through Celite, and concentrated in vacuo to provide the title aldehyde.

Provenance & Evidence