HCID 18700106, compound → HCID 54030415, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 4-(N-tert-butyloxy-carbonyl-4-piperidinyloxy)-2-trifluoromethylbenzoic acid (0.66 g, 2.3 mmol) from Step 2 above in THF (10 mL) at 0° C. was added BH3.THF complex (3.5 mL of a 1.0 M solution in THF, 3.5 mmol). The solution was stirred at 0° C. for 1 h and then at ambient temperature for 14 h. The solution was diluted with saturated aqueous NaHCO3 (25 mL) and the solvents were removed under reduced pressure. The residue was partitioned between EtOAc (50 mL) and water (2×25 mL). The organic phase was dried (MgSO4), filtered, and the solvent was removed under reduced pressure to give 4-(N-tert-butyloxycarbonyl-4-piperidinyloxy)-2-trifluoromethylbenzyl alcohol as a colorless gum (HPLC retention time=10.2 min (method A)).

Provenance & Evidence