Sodium hydride → 5-Benzyl-1-oxa-5-azaspiro[2.5]octane

Participants

Reaction Steps

Trimethylsulfonium iodide (2.13 g, 10.4 mmol) in DMSO (15 mL) was added to NaH (0.4907 g, 20.4 mmol) in DMSO (70 mL). 1-benzyl-3-piperidone hydrochloride hydrate (109) (0.996 g, 4.41 mmol) was taken up in DMSO (15 mL) and was added to the reaction mixture at room temperature. When the reaction was judged complete by TLC (0.5 h), the reaction was poured over ice and the product was extracted with CH2Cl2. The organics were washed with H2O, dried over sodium sulfate, filtered and concentrated in vacuo. Purification with alumina gel chromatography (900:100:3 CH2Cl2:Hexanes:2 N NH3 in EtOH) provided pure 5-benzyl-1-oxa-5-azaspiro[2,5]octane (110). 13C NMR (CDCl3): 137.54, 128.69, 127.83, 126.67, 62.55, 59.28, 53.32, 52.96, 52.48, 30.90, 23.51 ppm.

Provenance & Evidence