(S)-(5-Isobutyl-indan-2-yl)-carbamic acid benzyl ester → (S)-5-Isobutyl-indan-2-ylamine
Reaction equation
C(OC(=O)[NH:10][C@@H:11]1[CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[C:16]([CH2:20][CH:21]([CH3:23])[CH3:22])[CH:17]=2)[CH2:12]1)C1C=CC=CC=1>CO.[Pd]>[CH2:20]([C:16]1[CH:17]=[C:18]2[C:13](=[CH:14][CH:15]=1)[CH2:12][C@H:11]([NH2:10])[CH2:19]2)[CH:21]([CH3:23])[CH3:22]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
(S)-(5-Isobutyl-indan-2-yl)-carbamic acid benzyl ester ( ) is dissolved in methanol (100 ml), 10% Pd—C (200 mg) is added and the flask is purged with H2(g) (0.35 bar). The reaction mixture is stirred for 18 hours, the catalyst is filtered off. The solvent is removed in vacuo to give title compound. 1H nmr (CDCl3, 400 MHz); 7.10 (d, 1H), 7.00 (s, 1H), 6.90 (d, 1H), 3.85 (m, 1H), 3.15 (dd, 2H), 2.65 (dt, 2H), 2.45 (d, 2H), 1.80 (br m, 3H), 0.90 (d, 6H).