Fluorene-1-carboxylic acid → 1-(1-Fluorenecarbonyl)-3-(RS)-((4-phenyl)piperidin-1-yl)methyl-4-(SR)-phenylpyrrolidine

Participants

Reaction Steps

A solution of 10 mg (0.03 mnmol) of 3-(RS)-((4-phenyl)piperidin-1-yl)methyl-4-(SR)-phenylpyrrolidine (from Example 30, Step A), 10 mg (0.07 mmol) of DIEA and 10 mg (0.04 mmol) of bis (2-oxo-3-oxazolidinyl)phosphinic chloride (BOP-Cl) in 2 mL of CH2Cl2 (2 mL) at 0° C. was treated with 7 mg (0.16 mmol) of 1-fluorene carboxylic acid. The cooling bath was removed; the reaction was stirred at rt for 2 h and then was concentrated in vacuo . Preparative thin layer chromatography (silica gel GF, 20×20 cm, 1000 microns) using 95:5 v/v MeOH/CH2Cl2 as the eluant afforded 14 mg (88%) of the title compound as a foam. 1H NMR (500 MHz, CDCl3): δ7.12-7.87 (17H), 1.28-4.13 (19H). Mass Spectrum (NH3 -CI): 513 (M+1).

Provenance & Evidence