Sodium Bicarbonate → 5-(2-(2'-(Trifluoromethyl)biphenyl-4-yl)ethyl)indoline

Participants

Reaction Steps

The product of Step C (0.24 g, 0.65 mmol) was dissolved in AcOH (2 ml) and NaCNBH3 (0.082 g, 1.3 mmol) was added in portions. The mixture was stirred for 1 h and then poured into an aqueous solution of NaHCO3 and extracted with EtOAc (50 ml). The organic layer was separated, dried over MgSO4 and filtered. The filtrate was evaporated to dryness and the residue was purified by FCC (SiO2) to give the desired product (0.18 g, 75%), as pale paste. 1H-NMR (CDCl3) 2.81-2.94 (m, 4H); 3.0 (tr, 2H, J=7.22 Hz); 3.54 (tr, 2H, J=8.35 Hz); 6.58 (d, 1H, J=7.83 Hz); 6.84 (d, 1H, J=7.82 Hz); 6.9 (b, 1H); 7.17-7.21 (m, 3H); 7.31-7.35 (m, 2H); 7.43 (tr, 1H, J=7.65 Hz); 7.54 (tr, 1H, J=7.37 Hz); 7.72 (d, 1H, J=7.78 Hz).

Provenance & Evidence