Acetic Acid → HCID 67265876, compound

Participants

Reaction Steps

Add to a solution of (R)-4-((R)-4-benzyl-3-[2-(4-methoxy-2,6-dichloro-benzyl)-pent-4-enoyl]-oxazolidin-2-one (0.90 g, 2 mmol) in THF (20 mL) at room temperature 1-amino piperidine (0.40 g, 4 mmol) and acetic acid (0.2 mL). Stir the reaction at room temperature for 20 minutes and add sodium triacetoxy borohydride (1.69 g, 8 mmol) and continue stirring at room temperature for 12 h. Partition the mixture between ethyl acetate (20 mL) and water (20 mL). Separate the organic layer, wash three times with water (15 mL each) and then with brine (15 mL). After drying the organic layer over sodium sulfate, filter and concentrate under vacuum. Purify the residue by silica gel chromatography with 2:3 ethyl acetate/hexane to afford the free base of the title compound and then treat with 1 M HCl in ether to afford 0.34 g (43%): MS (m/z): 357 (M+).

Provenance & Evidence