193274-08-7

Basic information

• Product Name: {1-[2-(3a-(R)-benzyl-2-methyl-3-oxo-2,3,3a,4,6,7-hexahydro-pyrazolo[4,3-c]pyridin-5-yl)-1-(R)-benzyloxymethyl-2-oxo-ethylcarbamoyl]-1-methyl-ethyl}carbamic acid tert-butyl ester
• Synonyms: {1-[2-(3a-(R)-benzyl-2-methyl-3-oxo-2,3,3a,4,6,7-hexahydro-pyrazolo[4,3-c]pyridin-5-yl)-1-(R)-benzyloxymethyl-2-oxo-ethylcarbamoyl]-1-methyl-ethyl}carbamic acid tert-butyl ester
• CAS NO: 193274-08-7
• Molecular Weight: 605.734
• Mol File: 193274-08-7.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: {1-[2-(3a-(R)-benzyl-2-methyl-3-oxo-2,3,3a,4,6,7-hexahydro-pyrazolo[4,3-c]pyridin-5-yl)-1-(R)-benzyloxymethyl-2-oxo-ethylcarbamoyl]-1-methyl-ethyl}carbamic acid tert-butyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: {1-[2-(3a-(R)-benzyl-2-methyl-3-oxo-2,3,3a,4,6,7-hexahydro-pyrazolo[4,3-c]pyridin-5-yl)-1-(R)-benzyloxymethyl-2-oxo-ethylcarbamoyl]-1-methyl-ethyl}carbamic acid tert-butyl ester(193274-08-7)
• EPA Substance Registry System: {1-[2-(3a-(R)-benzyl-2-methyl-3-oxo-2,3,3a,4,6,7-hexahydro-pyrazolo[4,3-c]pyridin-5-yl)-1-(R)-benzyloxymethyl-2-oxo-ethylcarbamoyl]-1-methyl-ethyl}carbamic acid tert-butyl ester(193274-08-7)

Safety Data

• Hazardous Substances Data: 193274-08-7(Hazardous Substances Data)

Upstream product

• 193274-04-3 3a-(R)-Benzyl-2-methyl-2,3a,4,5,6,7-hexahydro-pyrazolo[4,3-c]pyridin-3-one 
• 159634-89-6 (R)-3-Benzyloxy-2-(2-tert-butoxycarbonylamino-2-methyl-propionylamino)-propionic Acid 
• 193274-37-2 (R)-3a-benzyl-2-methyl-4,5,6,7-tetrahydro-2H-pyrazolo[4,3-c]pyridin-3(3aH)-one (2R,3R)-2,3-dihydroxysuccinate 
• 1026087-20-6 3(R)-benzyloxy-2-(2-tert-butoxycarbonylamino-2-methyl-propionyl-amino)-propionic acid 
• 71760-04-8 propylphosphonic anhydride 
• 193274-00-9 3-(R,S)-Benzyl-4-oxo-piperidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-methyl ester 
• 161491-24-3 methyl 1-tert-butoxycarbonyl-4-oxo-3-piperidinecarboxylate 
• 108554-34-3 methyl 4-oxonipecotate 
• 193274-02-1 2,3a,4,5,6,7-hexahydro-2-methyl-3-oxo-3a-(phenylmethyl)-5H-pyrazolo[4,3-c]pyridine-5-carboxylic acid 1,1-dimethylethyl ester 

Downstream Products

• 193273-66-4 capromorelin 

Relevant articles and documents

Practical synthesis of capromorelin, a growth hormone secretagogue, via a crystallization-induced dynamic resolution

A practical synthesis of capromorelin (1), a growth hormone secretagogue, is described that utilizes as a key step a crystallization-induced dynamic resolution (CIDR) of (±)-3a-benzyl-2-methyl-4,5,6,7-tetrahydro-2H-pyrazolo[4,3-c]pyridin-3(3aH)-one [(±)-2] by L-tartaric acid salt formation, yielding (R)-2.L-tartaric acid in high chemical yield (>85%) and with diastereomeric excess (de) of ～98%. Treatment of (R)-2.L-tartaric acid with ammonium hydroxide provided (R)-2 without loss of chiral purity. In situ generated (R)-2 was coupled with (R)-3-(benzyloxy)-2-(2-(tert-butoxycarbonyl)-2-methylpropanamido)propanoic acid [(R)-3] to give predominantly a single diastereomer of N-Boc-protected capromorelin [(1R,3aR)-4]. This process was used to prepare bulk quantities of capromorelin from (±)-2 to support preclinical toxicology studies.

Process for preparing growth hormone secretagogues

This invention relates to improved processes for preparing compounds of Formula II, and compounds of Formula III, wherein R1, R2, R3 and Prt are defined as set forth in the specification.