(R)-(4-biphenylcarbonylamino)-2(R)-hydroxy-6-nitroindane → (R)-(4-biphenylcarbonylamino)-2(R)-hydroxy-6-aminoindane

反応式

[C:1]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:6]=[CH:5][C:4]([C:7]([NH:9][C@@H:10]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([N+:19]([O-])=O)[CH:17]=3)[CH2:12][C@H:11]2[OH:22])=[O:8])=[CH:3][CH:2]=1.[H][H]>[Pd].CN(C=O)C>[C:1]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:2]=[CH:3][C:4]([C:7]([NH:9][C@@H:10]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([NH2:19])[CH:17]=3)[CH2:12][C@H:11]2[OH:22])=[O:8])=[CH:5][CH:6]=1

参加物

実験手順

Combine 1 (R)-(4-biphenylcarbonylamino)-2(R)-hydroxy-6-nitroindane 55.7 g, 550 mL of DMF and 2.8 g of 10% Pd/C catalyst. Hydrogenate at 50 psi (345 kPa) of hydrogen at ambient temperature for 4.75 h. Filter the reaction mixture and dilute the filtrate with 1200 mL of water to give a slurry. Stir the slurry for 30 minutes, filter, wash with water, and dry in vacuo at 50° C. Combine the dried product and about 1 L of water and slurry for 30 minutes, filter, wash with water, and dry in vacuo at 50° C. to afford 45.4 g (90%) of 1 (R)-(4-biphenylcarbonylamino)-2(R)-hydroxy-6-aminoindane: 1R (KBr, cm−1); 3584, 3364, 3277, 1632, 1543, 1326, 1073, 743; HRMS calc'd for C22H20N2O2: 344,4120; Found: 344,1525.