3-hydroxy-3-phenylbutanenitrile

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 3-hydroxy-3-phenylbutanenitrile (1 g, 6.2 mmol) in THF (10 mL) was added dropwise BH3.Me2S (32 mL, 62 mmol) under a N2 atmosphere. The mixture was stirred at rt overnight. The reaction was quenched with MeOH (10 mL). The mixture was concentrated to give crude 4-amino-2-phenylbutan-2-ol (1.2 g, crude), which was used in the next step without further purification. The reaction was quenched with MeOH (10 mL) The mixture was concentrated

Conditions: temp:-20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Dry THF was cooled to −20° C. and 2.5 M n-Bull (100 mL, 0.25 mol) was added. A solution of CH3CN (11.25 g, 0.25 mol) in dry THF was added dropwise over 10 min. Then the mixture was stirred for 1 h at −20° C. and a solution of acetophenone (30 g, 0.25 mol) in THF was added dropwise over 10 min. The mixture was stirred at −20° C. for 15 min and warmed to rt over 15 min. Aq NH4Cl was added to quench the reaction. The solution was extract with EtOAc. The organic layer washed with brine, dried over anhydrous Na2SO4 and concentrated to give 3-hydroxy-3-phenylbutanenitrile (30 g, yield 75%). 1H NMR (CDCl3, 400 MHZ): δ=1.76 (s, 3H), 2.83 (s, 2H), 7.34 (m, 1H), 7.41 (m, 2H), 7.5 (m, 2H). 2.5 M n-Bull (100 mL, 0.25 mol) was added The mixture was stirred at −20° C. for 15 min warmed to rt over 15 min to quench the reaction The solution was extract with EtOAc The organic layer washed with brine dried over anhydrous Na2SO4 concentrated