Toluene → HCID 67189504, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of potassium ferricyanide (0.06 mmol, 3.0 equiv.), potassium carbonate (0.06 mmol, 3.0 equiv.), and (DHQD)2PHAL (0.0006 mmol, 0.03 equiv.) is treated with a solution of water/tert-butyl alcohol (5 mL, 1:1) and is stirred at 25° C. for 5 min. The reaction mixture is treated with a 0.2 M solution of osmium tetroxide in toluene (0.0002 mmol, 0.01 equiv.) and cooled to 0° C. To this is added 2-(R)-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-N-[1-(3-methyl-but-2-enyl)-1H-pyrazol-3-yl]-propionamide (prepared as in Example 51, 0.02 mmol, 1 equiv.) and methane sulfonamide (0.02 equiv.). The heterogeneous mixture is stirred at 0° C. for 20 h. After such time the cooling bath is removed and the mixture is treated while stirring with ethyl acetate (15 mL) and sodium sulfite (0.36 mmol, 18 equiv.). To this solution is added water (20 mL) and the phases are separated. The aqueous phase is backextracted with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo. Purification on an AnaLogix Intelliflash system would produce (R)-2-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-N-[1-(2,3-dihydroxy-3-methyl-butyl)-1H-pyrazol-3-yl]propionamide as a single diastereomer of unknown stereochemistry at the hydroxyl carbon center but opposite configuration at the hydroxyl stereocenter of Example 132.

Provenance & Evidence