反应详情

To a degassed solution of (+/−)-tert-butyl ((1R,5S,65)-6-hydroxy-5-methyl-3-(3-nitropyridin-4-yl)cyclohex-2-en-1-yl)carbamate (1.0 equiv.) in i-PrOH (0.07 M) was added Pd/C (0.1 equiv.). The solution was degassed and purged to H2 and left stirring under a balloon of H2 at rt for 16 hrs. The solution was degassed and purged to Ar, diluted with CH2Cl2, filtered through a pad of celite, concentrated and purified by ISCO SiO2 chromatography. Purification was completed via SFC (20% MeOH, 100 mL/min, AD column) to yield tert-butyl ((1S,2R,3R,5S)-5-(3-aminopyridin-4-yl)-2-methoxy-3-methylcyclohexyl)carbamate (42% yield, 99% ee) and tert-butyl ((1R,2S,3S,5R)-5-(3-aminopyridin-4-yl)-2-methoxy-3-methylcyclohexyl)carbamate (39% yield, 99% ee). LC/MS (m/z)=336.2 (MH+), Rt=0.67 min. 1H NMR (400 MHz, <cdcl3>) δ ppm 1.08 (d, J=7.04 Hz, 3 H), 1.43-1.49 (m, 10 H), 1.52-1.64 (m, 2 H), 1.70-1.81 (m, 2 H), 2.52-2.64 (m, 1 H), 3.39 (br. s., 1 H), 3.52-3.57 (m, 3 H), 3.62 (br. s., 2 H), 3.66-3.75 (m, 1 H), 4.75-4.87 (m, 1 H), 6.98 (d, J=5.09 Hz, 1 H), 7.95-8.05 (m, 2 H).

1. customThe solution was degassed
2. custompurged to H2
3. waitleft
4. customThe solution was degassed
5. custompurged to Ar
6. additiondiluted with CH2Cl2
7. filtrationfiltered through a pad of celite
8. concentrationconcentrated
9. custompurified by ISCO SiO2 chromatography
10. customPurification