Sodium hydride → HCID 91618405, compound

Participants

Reaction Conditions

Reaction Steps

Sodium hydride (197 mg, 4.92 mmol) was added to a solution of tert-butyl [1-(1,2-dihydroxyethyl)cyclopropyl]carbamate (100 mg, 0.46 mmol) in THF (1 mL) at room temperature. The mixture was stirred at 30° C. under a nitrogen atmosphere for 16 hours. After being cooled to 20° C., the mixture was diluted with ice water (1 mL) and then extracted with ethyl acetate. The organic layer was dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by chromatography on silica gel (methanol/dichloromethane) to give 7-(hydroxymethyl)-6-oxa-4-azaspiro[2.4]heptan-5-one. 1H NMR (300 MHz, DMSO-d6): δ 7.62 (br s, 1H), 5.00-4.96 (m, 1H), 4.40-4.35 (m, 1H), 3.51-3.40 (m, 2H), 1.01-0.88 (m, 1H), 0.80-0.55 (m, 3H).

Provenance & Evidence