反应详情

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%).

1. filtrationThe catalyst was filtered off over Hyflo Super Cell and solvents
2. customwere evaporated under reduced pressure
3. additionThe resulting residue was treated with HCl until all of the amine
4. additiondiluted with water
5. customuntil partitioned
6. extractionThe non-basic organics were extracted into diethyl ether (2×100 ml)
7. extractionOrganics were then extracted into CH2Cl2 (5×100 ml)
8. dry with materialthe combined extracts were dried over MgSO4
9. concentrationConcentration