Triphenylphosphine → HCID 57304174, compound

Participants

Reaction Steps

To a solution of (2S,4R)-N-tert-butoxycarbonyl-2-[(R)-3-(N-tert-butoxycarbonyl-N-methylamino)-1-hydroxypropyl]-4-hydroxypyrrolidine (1.0 g, 2.67 mmol, intermediate prepared in REFERENCE EXAMPLE 27-2) in tetrahydrofuran (10 ml) were successively added triphenylphosphine (842 mg, 3.21 mmol) and diethyl azodicarboxylate (0.505 ml, 3.21 mmol) under a nitrogen atmosphere under cooling with ice. The mixture was stirred at the same temperature for 10 minutes, and then thioacetic acid (0.25 ml, 0.35 mmol) was dropwise added thereto. The reaction solution was stirred at the same temperature for 2.5 h and then concentrated in vacuo. A mixture (10 ml) of hexane-ethyl acetate (5:1) was added to the residue. The precipitate was filtered off, and the filtrate was concentrated in vacuo. The residue was subjected to silica gel column chromatography (Wakogel™ C-300, hexane-ethyl acetate=5:1) to give (2S,4R)-N-tert-butoxycarbonyl-4-acetylthio-2-[(R)-3-(N-tert-butoxycarbonyl-N-methylamino)-1-hydroxypropyl]pyrrolidine (1.03 g, yield: 89.2%). The data of this compound agreed with those of the compound prepared in REFERENCE EXAMPLE 27-2. ##STR411##

Provenance & Evidence