(R)-N-(4-Dodecylphenylsulfonyl)pyrrolidine-2-carboxaMide synthesis

Yield: 86%

Reaction Conditions:

with hydrogen;palladium 10% on activated carbon in methanol at 20; for 24 h;

Steps:

5
Example 5 Sulfonamide ent-15: To a solution of Z-D-sulfamide (4.99 g, 8.97 mmol) in MeOH (178 mL) was added 10% Pd/C (536 mg). The mixture was stirred at rt for under an atmosphere of hydrogen. After 24 hours, the reaction was filtered through Celite and silica gel pad, and the filtrate was concentrated in vacuo to give white solid. The crude product was purified by chromatography over silica gel, eluting with 10% MeOH/CH₂Cl₂, to give the product ent-15 (3.26 g, 7.73 mmol, 86%) as a white solid. Mp: 184-186° C.; [α]_D²³=+94° (c=0.95, CHCl₃). IR (neat) 3135, 2955, 2920, 2852, 1626, 1458, 1372, 1308, 1144, 1084, 843 cm^-1; ¹H NMR (400 MHz, CDCl₃) 8.73 (br s, 1H), 8.06 (br s, 1H), 7.85 (d, J=8.0 Hz, 2H), 7.22-7.26 (m, 2H), 4.33 (t, J=8.0 Hz, 1H), 3.23-3.43 (m, 2H), 2.33-2.40 (m, 1H), 0.82-2.05 (m, 28H); ¹³C NMR (75 MHz, CDCl₃) δ 173.8, 140.4, 127.8, 127.2, 126.4, 62.8, 47.8, 39.9, 38.2, 36.8, 31.9, 31.8, 30.1, 29.7, 29.6, 29.3, 29.2, 27.6, 27.2, 24.5, 22.7, 14.1; HRMS (EI+) calcd. for C₂₂H₃₉N₂O₃S (M+1), 423.2681 found 423.2701.

References:

The State of Oregon acting by and through the State Board of Higher Education on behalf of Orego US2010/184986, 2010, A1 Location in patent:Page/Page column 45