4-(3-Phenylpropyl)piperidine → 2-(R)-(3-(S)-((4-(3-Phenylpropyl)piperidin-1-yl)methyl)-4-(S)-phenylpyrrolidin-1-yl)-2-(cyclohexyl)acetic acid, benzyl ester

Participants

Reaction Steps

To a solution of 34 mg (0.084 mmol) of 2-(R)-(3-(R)-formyl-4-(S)-phenylpyrrolidin-1-yl)-2-(cyclohexyl)acetic acid, benzyl ester (from EXAMPLE 1, Step I) and 19 mg (0.093 mmol) of 4-(3-phenylpropyl) piperidine in 2 mL of CH2Cl2 at rt was added 27 mg (0.13 mmol) of sodium triacetoxyborohydride. After stirring for 1 h, the reaction was diluted with 25 mL of CH2Cl2 and washed with 25 mL of sat'd NaHCO3. After separating the phases, 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 MgSO4 and concentrated. The residue was purified by flash chromatography eluting with 50:1 v/v CH2Cl2/MeOH to give 37 mg (74%) of the title compound: 1H NMR (500 MHz) δ 0.99-2.91 (32H), 3.20-3.27 (3H1), 5.19 (ABq, J=19.7, 2H), 7.17-7.43 (15H); NH3-CI-MS 593 (M+H).

Provenance & Evidence