Borane;tetrahydrofuran → tert-Butyl 4-[2-(hydroxymethyl)phenyl]piperazine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-Boc-4-(2-carboxy-phenyl)-piperazine from Step 1 in 340 mL of THF at 0° C. was added BH3-THF (120 mL of a 1 M solution in THF). The cold bath was removed, and the solution stirred overnight. The solution was cooled to about 0° C. and then 60 mL of 2 M NaOH was added followed by EtOAc and brine. After separation, the aqueous solution was extracted with EtOAc (3×). The combined organic solutions were washed with water (2×) and brine, and then dried (Na2SO4), filtered and concentrated to give about 11.2 g (38.3 mmol, 96%) of the title compound. LRMS (ESI+): 393.2 [M+1]

Provenance & Evidence