Reaction Steps
A mixture of (R)-tert-butyl 2-(7-(benzyloxy)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetate (0.320 g, 0.848 mmol), Pd(OAc)2 (0.019 g, 0.085 mmol) and ammonium formate (0.214 g, 3.39 mmol) in methanol (20 mL) was heated under reflux overnight. After cooling the mixture was filtered through celite and then the solvent was removed under reduced pressure. Water (10 mL) and DCM (10 mL) were added and the 2 layers separated. The aqueous layer was extracted with DCM then the combined organics dried by passing through a phase separator cartridge. The solvent was removed under reduced pressure to give (R)-tert-butyl 2-(7-hydroxy-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetate (0.240 g, 0.835 mmol, 99% yield, >70% ee) as a colorless oil. Exact mass calculated for C17H21NO3: 287.2, found: LCMS m/z=288.2, [M+H+]; 1H NMR (400 MHz, CDCl3) δ ppm 1.56 (s, 9 H), 3.40 (m, 2 H), 4.13 (t, J=6.6 Hz, 2 H), 5.11 (s, 2 H), 5.80 (s, 1 H), 7.00 (dd, J1=9.0, J2=2.2 Hz, 1 H), 7.18 (m, 2 H), 7.33 (m, 1 H), 7.39 (m, 2 H), 7.48 (m, 2 H), 7.55 (s, 1 H) 1H NMR (400 MHz, d6-DMSO) δ ppm 1.44 (s, 9 H), 2.18 (m, 1 H), 2.52 (dd, J1=15.9, J2=7.7 Hz, 1 H), 2.62 (dd, J1=15.9, J2=7.1 Hz, 1 H), 2.74 (m, 1 H), 3.54 (m, 1 H), 3.91 (m, 1 H), 4.05 (ddd, J1=9.8, J2=8.5 Hz, J3=4.3 Hz 1 H), 5.88 (s, 1 H), 6.54 (m, 1 H), 6.76 (d, J=2.3 Hz, 1 H), 7.06 (d, J=8.6 Hz, 1 H), 8.54 (s, 1 H).
