1474047-52-3

Upstream product

• 705949-06-0 C₁₆H₂₅NO₃ 
• 35182-62-8 (1S,2S,5R,7S)-2,8,8-trimethyl-3-azatricyclo[5.1.1.0^2,5]nonan-4-one 
• 1148-11-4 N-Benzyloxycarbonyl-L-proline 
• 1474047-48-7 methyl (S)-2-{(1S,2S,3R,5S)-2-amino-2,6,6-trimethylbicyclo[3.1.1]heptan-3-ylcarboxamido}-3-phenylpropanoate 
• 61350-60-5 (S)-benzyloxycarbonyl-proline acid chloride 
• 1474047-44-3 methyl (S)-2-{(1S,2S,3R,5S)-2-[(tert-butoxycarbonyl)amino]-2,6,6-trimethylbicyclo[3.1.1]heptan-3-ylcarboxamido}-3-phenylpropanoate 
• 7785-70-8 (+)-α-pinene 
• 705949-07-1 C₁₆H₂₇NO₄ 

Downstream Products

• 1474047-56-7 (S)-3-phenyl-2-{(1S,2S,3R,5S)-2,6,6-trimethyl-2-[(S)-pyrrolidin-2-ylcarboxamido]bicyclo[3.1.1]heptan-3-ylcarboxamido}propanoic acid 
• 1474047-55-6 (S)-2-{(1S,2S,3R,5S)-2-{(S)-1-[(benzyloxy)carbonyl]pyrrolidin-2-ylcarboxamido}-2,6,6-trimethylbicyclo[3.1.1]heptan-3-ylcarboxamido}-3-phenylpropanoic acid 

Relevant academic research and scientific papers

Stereoselective synthesis of chiral pyrrolidine derivatives of (+)-α-pinene containing a β-amino acid moiety

We report the synthesis of several enantiopure pyrrolidine derivatives containing a β-amino acid moiety. These novel chiral compounds were prepared through stereospecific chlorosulfonyl isocyanate (CSI) addition to the readily available, natural terpene (+)-α-pinene. Coupling of N-Boc-protected β-amino acid derivatives with various bulky amines and amino acids using the mixed anhydride activation method, followed by N-deprotection, afforded the corresponding chiral amino amides in good yields. Despite the severe steric hindrance anticipated in α-pinene-based heterocycles, efficient coupling of the amino amides and an amino ester with the acyl chloride of N-Cbz-protected (S)-proline provided the corresponding pyrrolidinic pinene derivatives in good yields. Moreover, a convenient synthesis of N-Cbz- and N-Boc-monoprotected (S)-prolinamine is reported. Georg Thieme Verlag Stuttgart New York.