反应详情

A solution of 8.5 g of 47c in 25 mL of acetic acid and 250 mL of THF is hydrogenated at 48 psi of hydrogen over 0.5 g of (bicyclo(2.2.1.)hepta-2,5-diene[ 2S,3S]bis(diphenylphosphino)butane)rhodium(I) perchlorate for 18 h. The reaction is filtered and evaporated to a residue. The residue is chromatographed using variable gradient hexane-ethyl acetate to give 7.9 g of reduced product as a residue. Multiple crystallizations give 2.6 g of diastereomerically pure 40c. NMR(CDCl3) δ1.40(d,J=6 Hz,3H); 1.43(s,9H); 1.60-1.97(m,6H); 3.73(s,3H); 3.74(s,3H); 4.12-4.37(m,2H); 4.52-4.61(m,1H); 5.12(bs,3H); 5.44-5.55-(b s,1H); 6.73(b s,1H); 7.36(b s,5H); 13C-NMR: δ18.02(CH--CH3); 21.12(CH2 --CH2 --CH2); 28.23(--OC(CH3)3); 31.87(--CH2 --CH2); 32.29(--CH2CH2 --); 47.99(--CHCH3); 52.23(--OCH3); 52.38(--OCH3); 52.75 (OCCHN); 54.41(OCCHN); 67.01(--OCH2Ar); 79.97(--OC(CH3)3); 127.99 (phenyl ring carbon); 128.09 (phenyl ring carbon); 128.44(ArCH); 136.13(ArCC); 155.48(OCONH); 156.23(OCONH); 171.10(--CONH--); 173.03(--CO2 --2X); IR(KBr)(cm-1): 3340(s); 1760(s); 1740(s); 1680(s); 1660(s); 1660(s); 1520(s); MS(FAB) m/z 546(M+Na)+ ; 524(MH)+ ; 424(MH--C4H8CO2)+ ; Anal. Calcd: C, 57.35;H, 7.12; N, 8.03; Found: C, 57.23;H, 7.27; N, 8.03; rotation [α]D25 -9±1; m.p. 120°-121° C.

1. customfor 18 h
2. filtrationThe reaction is filtered
3. customevaporated to a residue
4. customThe residue is chromatographed