4-Toluenesulfonyl chloride → tert-Butyl 5-cyano-1,3-dihydro-2H-isoindole-2-carboxylate
Reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:17]([NH2:19])=O)[CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1(C)C=CC(S(Cl)(=O)=O)=CC=1>N1C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:17]#[N:19])[CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of N-t-butoxycarbonyl-5-aminocarbonylisoindoline (D14) (140 mg) in pyridine (3 ml) at rt was treated with 4-toluenesulfonyl chloride (305 mg) and then stirred overnight. Following evaporation the residue was dissolved in EtOAc (10 ml), washed with saturated NaHCO3 solution (10 ml), water (10 ml), brine (10 ml), dried (MgSO4) and concentrated. The residue was chromatographed on a silica gel flash column [step gradient 5-20% EtOAc in light petroleum 40-60] to give the title compound (D15) (0.64 g). MS electrospray (+ion) 189 (MH+-t-Bu). 1H NMR δ (CDCl3): 7.56 (2H, m), 7.38 (1H, m), 4.71 (4H, m), 1.52 (9H, s).