(2S,3S)-3-(tert-butoxycarbonyl)piperidine-2-carboxylic acid synthesis

Yield:-

Steps:

Multi-step reaction with 5 steps
1.1: 90 percent / K₂CO₃ / dimethylformamide; dimethylsulfoxide / 50 °C
2.1: KHMDS / tetrahydrofuran; toluene / 1 h / -78 °C
2.2: 75 percent / tetrahydrofuran / -78 - 30 °C
3.1: 9-BBN / tetrahydrofuran / 20 °C
3.2: 78 percent / aq. NaOAc; 33percent H₂O₂ / 3 h / 20 °C
4.1: 75 percent / PDC / CH₂Cl₂ / 48 h / 20 °C
5.1: 95 percent / H₂ / 10percent Pd-C / methanol / 2585.81 Torr

References:

Xue, Chu-Biao;He, Xiaohua;Roderick, John;Corbett, Ronald L.;Decicco, Carl P. [Journal of Organic Chemistry,2002,vol. 67,# 3,p. 865 - 870]