Aluminium lithium hydride → HCID 67125907, compound

Participants

Reaction Steps

Lithium aluminum hydride (312 mg, 8.2 mmol) was stirred in THF (35 mL) at 0° C. (S)-1-(tert-butoxycarbonyl)-5,5-dimethylpyrrolidine-2-carboxylic acid (500 mg, 2.1 mmol) in THF (5 mL) was added dropwise over 15 min. The resulting mixture was stirred at rt for 1 h, and heated at 55° C. for 1 h. Another batch of lithium aluminum hydride (140 mg, 3.7 mmol) was added and the resulting mixture was heated at 60° C. for 2 h. LC-MS indicated partial conversion to the product. The reaction mixture was cooled to 0° C. and quenched with 0.5 mL of H2O, 0.5 mL of 10% NaOH, and 1.5 mL of H2O sequentially. The resulting mixture was stirred at rt for 30 min before it was filtered through a celite plug. The filtrate was evaporated under reduced pressure to give crude (S)-(1,5,5-trimethylpyrrolidin-2-yl)methanol (380 mg) as a clear oil. LC-MS (ESI) m/z 144 (M+H)+.

Provenance & Evidence