Lithium borohydride → HCID 86591375, compound

Participants

Reaction Steps

Lithium borohydride (56 mg) was added in a single portion to a stirred solution of the product from Step 2 (1.0 g) in dry THF. (20 mL). The resulting solution was stirred at room temperature for 18 hrs, quenched with NH4Cl (aq. satd 50 mL) and extracted into DCM. The organic extract was dried over MgSO4, filtered and the solvent removed under reduced pressure and the product purified by flash chromatography over silica (200–400 mesh, 10–60% EtOAc/isohexane) to give [5-(2-hydroxy-ethoxy)tricyclo [8.2.1.03,8]trideca-3,5,7-trien-13-yl]-carbamic acid tert-butyl ester as a white solid (340 mg). 1H NMR (CDCl3 400 MHz), δ 1.20 (2H, m), 1.47 (9H, s), 1.69 (2H, m), 2.04 (1H, m), 2.50 (4H, m), 2.96 (2H, m), 3.94 (2H, m), 4.05 (3H, m), 4.99 (1H, brm), 6.62 (1H, dd, J=8.0, 1.0 Hz), 6.67 (1H, d, J=1.0 Hz), 6.98 (1H, d, J=8.0 Hz).

Provenance & Evidence