Scheme 2.
Synthetic pathway leading to final compounds 8–21: (i) (S)-3-amino-1-Boc-pyrrolidine or (S)-2-(aminomethyl)pyrrolidine or (R)-2-(aminomethyl)pyrrolidine or (S)-3-(aminomethyl)pyrrolidine or (R)-3-(aminomethyl)pyrrolidine, acetonitrile, 140 °C, 7 h MW; (ii) 3-chlorobenzyl sulfonyl chloride, BTPP, DCM, 0 °C-rt; (iii) 1M HCl/MeOH; (iv) aldehyde: (S)-2-hydroxypropanal or (R)-2-hydroxypropanal or glycoaldehyde or 3-methoxypropanal or 3,3,3-trifluoropropanal or acetaldehyde or isobutyraldehyde, NaBH3CN, EtOH, rt, 12 h.
