Hydrochloric Acid → Cyclohexyl-{(S)-3-[4-hydroxy-4-(3-phenyl-propyl)-piperidin-1-ylmethyl]-4-phenyl-pyrrolidin-1-yl}-acetic acid benzyl ester

Participants

Reaction Steps

A solution of 87 mg (0.21 mmol) of 2-(R)-(3-(R)-formyl-4-(S)-phenylpyrrolidin-1-yl)-2-(cyclohexyl)acetic acid, benzyl ester (from EXAMPLE 1, Step I) and 69 mg (0.26 mmol) of 4hydroxy-4-(3-phenylpropyl)-piperidine.HCl in 5 mL of CH2Cl2 at rt was treated with 0.045 mL (0.25 mmol) of DIEA and 86 mg (0.40 mmol) of sodium triacetoxyborohydride and stirred at rt for 1 h. The reaction was diluted with 25 mL of CH2Cl2 and washed with 25 mL of 1.0 N NaHCO3. The layers were separated and the aqueous layer was extracted with 25 mL of CH2Cl2. The combined organic phases were washed with 50 mL of sat'd NaCl, dried over Na2SO4 and concentrated. Flash chromatography on silica gel using 50:1 v/v CH2Cl2/MeOH as the eluant afforded 110 mg (83%) of the title compound: RF: 0.46 (20:1 v/v CH2Cl2/MeOH); 1H NMR (300 MHz) δ 0.91-2.85 (m, 32H), 3.16-3.27 (m, 3H), 5.15 (ABq, J=12.2 Hz, 2H), 7.15-7.41 (m, 15H); NH3-CI-MS 609 (M+H).

Provenance & Evidence