(4S)-4-(2-methylpropyl)-5,5-diphenyl-1,3-oxazolidin-2-one

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A suspension of (S)-4-isobutyl-5,5-diphenyl-2-oxazolidinone 17 (7.6 g, 25.6 mmol) in MeOH/AcOH and a 10% Pd (282 mg, 2.6 mmol) on activated carbon was shaken for 93 h under 4–5 atm pressure of hydrogen at room temperature. The catalyst was filtered off over Hyflo Super Cell and solvents were evaporated under reduced pressure. The resulting residue was treated with HCl until all of the amine was converted to its HCl salt, stirred overnight at room temperature and diluted with water until partitioned occurred. The non-basic organics were extracted into diethyl ether (2×100 ml) and then the aqueous layer was made basic with NaOH pellets. Organics were then extracted into CH2Cl2 (5×100 ml) and the combined extracts were dried over MgSO4. Concentration gave the title product 18 (5.7 g, 87%) as a white amorphous solid. m.p. 46–48° C. [α]D25=−31.6° (c, 4.12 CHCl3). δH 0.86 (6H, dt, J=6.60 and 2.10 Hz, CH3), 1.00–1.50 (4H, m and broad s, CH2 and NH2), 1.66–1.86 (1H, m, CH), 3.61 (2H, broad s, CH—NH2 and CH—Ph2), 7.10–7.40 (10H, m, Ar—H). δC 21.8 and 24.7 (CH3), 25.5 (CH), 45.6 (CH2), 52.4 (CH—NH2), 61.6 (CH—Ph2), 126.9, 127.1, 128.8, 129.0, 129.2, 129.4, 143.8, 144.0 (Ar). Accurate mass (CI): Found 254.190200; Calculated for (MH+) C18H24N 254.190875 (2.7 ppm). νmax (cm−1): 3368 (N—H), 3057, 3027 (Ar C—H), 2951, 2932, 2909, 2867 (methyl and methylene C—H), 1595, 1494, 1450 (Ar C═C). m/e (CI) 254 (MH+, 100%). The catalyst was filtered off over Hyflo Super Cell and solvents were evaporated under reduced pressure The resulting residue was treated with HCl until all of the amine diluted with water until partitioned The non-basic organics were extracted into diethyl ether (2×100 ml) Organics were then extracted into CH2Cl2 (5×100 ml) the combined extracts were dried over MgSO4 Concentration

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Trichloromethyl chloroformate (13.0 g, 65.8 mmol) was added to a mixture of (S)-2-amino-1,1-diphenyl-4-methylpentan-1-ol 16 (12.4 g of 65%, 29.9 mmol) and triethylamine (12.7 g, 125.5 mmol) in CH2Cl2 at 0° C. The reaction mixture was stirred for 15 h, allowing to warm to room temperature. The mixture was then washed with HCl (3×200 ml) and water (2×200 ml), and dried over MgSO4. Concentration gave a crude product, which was washed with diethyl ether to afford the title compound 17 (7.9 g, 90%) as a white solid. m.p. 212–214° C. [α]D25=−286.1° (c, 4.32 in CHCl3). δH 0.85 (3H, d, J=6.6 Hz, CH3), 0.91 (3H, d, J=6.6 Hz, CH3), 0.96–1.08 (2H, m, CH2), 1.53–1.73 (1H, m, CH—Me2), 4.57 (1H, dd, J=10.5 and 3.60 Hz, CH—NH), 7.05 (1H, s, NH), 7.16–7.50 (10H, m, Ar—H). δC 20.8, 23.7, 24.9, 41.8, 58.8, 89.1, 125.9, 126.3, 127.6, 127.8, 128.1, 128.3, 139.3, 142.5 (Ar), 158.8 (C═O). νmax (cm−1): 3261, 3160 (N—H), 2955, 2869 (methyl and methylene C—H), 1752, 17235 (C═O), 1495, 1447 (Ar C═C), 1251 (C—O). m/e 313 (MNH4+, 12%), 296 (MH+, 15%), 237 (100%). The mixture was then washed with HCl (3×200 ml) and water (2×200 ml) dried over MgSO4 Concentration gave a crude product, which was washed with diethyl ether