Acetic Acid → HCID 67280601, compound

Participants

Reaction Steps

To a solution of tert-butyl 4-[(2S,3S)-3-[(4-fluorobenzoyl)amino]-2-hydroxy-indan-5-yl]piperazine-1-carboxylate (300 mg, 0.659 mmol) in 1,4-dioxane (5.0 mL), add 4 M hydrogen chloride in dioxane (5.0 mL) at room temperature and stir for 1 hr. Concentrate the suspension in vacuo. Add to the residue saturated aqueous sodium bicarbonate (50 mL) and extract with ethyl acetate (3×50 mL). Wash the combined organic layers with brine, dry over sodium sulfate, and concentrate in vacuo. Dissolve the residue in methanol (20 mL) and add 3-oxetanone (142 mg, 1.98 mmol), glacial acetic acid (170 μL, 2.96 mmol), and crushed activated 4 Å molecular sieves. Stir the resulting suspension at 50° C. for 1 hr. Add sodium cyanoborohydride (131 mg, 1.98 mmol) at room temperature and stir overnight. Add a saturated sodium bicarbonate solution (20 mL) and stir for 20 min. Extract with dichloromethane (3×50 mL) and wash the combined organic layers with water and brine. Dry the organic portion over sodium sulfate, filter, and concentrate to obtain the title compound (220 mg, 81%). LC-ES/MS m/z 412 [M+H]+.

Provenance & Evidence