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A flask was charged with 1-(tert-butoxycarbonyl)-4-(pyridin-3-yl)piperidine-4-carboxylic acid (4.0 g, 13.1 mmol) and tetrahydrofuran (25 mL). The reaction was placed under nitrogen. To the flask was added borane-tetrahydrofuran complex (1 M in tetrahydrofuran, 26.1 mL, 26.1 mmol) and heated at reflux for 2 h. The reaction was cooled to 0° C. and quenched with methanol (100 mL). The solution was then concentrated in vacuo. The residue was purified via column chromatography (5% methanol/95% dichloromethane) to yield 3.2 g (84%). Mass Spec.: 293.26 (MH)+. LC: tr=1.65 min (Phenomenex-Luna 4.6×50 mm S10, 10% MeOH/90% H2O/0.1% TFA→90% MeOH/10% H2O/0.1% TFA Gradient Time=2 min, Flow rate=4 mL/min).

1. temperatureheated
2. temperatureat reflux for 2 h
3. customquenched with methanol (100 mL)
4. concentrationThe solution was then concentrated in vacuo
5. customThe residue was purified via column chromatography (5% methanol/95% dichloromethane)
6. customto yield 3.2 g (84%)