M. Morimoto, K. Sakai
Jun 30, 2008
Citations
0
Influential Citations
2
Citations
Journal
Tetrahedron-asymmetry
Abstract
Abstract The synthesis of ( S )-1-benzyl-3-hydroxypyrrolidine ( S )- 5 comprised the asymmetric hydroboration of 1-benzyl-3-pyrroline 4 , followed by oxidation and chiral purification via diastereomeric salt formation. The asymmetric borane reagent was generated ‘in situ’ from NaBH 4 , BF 3 –OEt 2 , and (+)-α-pinene 1 (85% ee) and reacted with 4 , prepared from cis -1,4-butenediol 3 , to give crude product ( S )- 5 . The following chiral purification via diastereomeric salt formation proceeded to afford ( S )- 5 with >99% ee. The optimized process was successfully scaled up to an industrial scale to produce a 252 kg batch of ( S )- 5 .