176966-76-0

Basic information

• Product Name: (5S)-5-tert-butyldiphenylsilyloxy-piperidine-2-one
• Synonyms: (5S)-5-tert-butyldiphenylsilyloxy-piperidine-2-one
• CAS NO: 176966-76-0
• Molecular Weight: 353.536
• Mol File: 176966-76-0.mol

Chemical Properties

• CAS DataBase Reference: (5S)-5-tert-butyldiphenylsilyloxy-piperidine-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (5S)-5-tert-butyldiphenylsilyloxy-piperidine-2-one(176966-76-0)
• EPA Substance Registry System: (5S)-5-tert-butyldiphenylsilyloxy-piperidine-2-one(176966-76-0)

Safety Data

• Hazardous Substances Data: 176966-76-0(Hazardous Substances Data)

Upstream product

• 24211-54-9 (S)-5-hydroxypiperidin-2-one 
• 58479-61-1 tert-butylchlorodiphenylsilane 

Downstream Products

• 176966-77-1 tert-butyl (5S)-5-tert-butyldiphenylsilyloxy-piperidine-2-one-1-carboxylate 
• 477600-74-1 tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate 
• 1259404-17-5 tasocitinib 
• 176966-79-3 (4R,5S)-5-(tert-Butyl-diphenyl-silanyloxy)-4-methyl-2-oxo-piperidine-1-carboxylic acid tert-butyl ester 
• 176966-83-9 (3S,4S)-3-(tert-Butyl-diphenyl-silanyloxy)-4-[2-(2-methoxy-ethoxymethoxy)-ethyl]-piperidine-1-carboxylic acid tert-butyl ester 
• 176966-94-2 (4S,5S)-5-(tert-Butyl-diphenyl-silanyloxy)-4-(4-chloro-phenyl)-2-oxo-piperidine-1-carboxylic acid tert-butyl ester 
• 176966-95-3 (4S,5S)-5-(tert-Butyl-diphenyl-silanyloxy)-4-(4-fluoro-phenyl)-2-oxo-piperidine-1-carboxylic acid tert-butyl ester 
• 176966-96-4 (3S,4S)-3-(tert-Butyl-diphenyl-silanyloxy)-4-(4-chloro-phenyl)-piperidine-1-carboxylic acid tert-butyl ester 
• 176966-97-5 (3S,4S)-3-(tert-Butyl-diphenyl-silanyloxy)-4-(4-fluoro-phenyl)-piperidine-1-carboxylic acid tert-butyl ester 
• 176966-81-7 (4R,5S)-5-(tert-Butyl-diphenyl-silanyloxy)-2-oxo-4-(2-oxo-ethyl)-piperidine-1-carboxylic acid tert-butyl ester 
• 176966-92-0 (4R,5S)-4-Allyl-5-(tert-butyl-diphenyl-silanyloxy)-2-oxo-piperidine-1-carboxylic acid tert-butyl ester 
• 176966-82-8 (3S,4S)-3-(tert-Butyl-diphenyl-silanyloxy)-4-(2-hydroxy-ethyl)-piperidine-1-carboxylic acid tert-butyl ester 
• 176966-80-6 tert-butyl (5S)-5-(tert-butyldiphenylsilyloxy)-4-methyl-2H-2-oxo-5,6-dihydro-piperidine-1-carboxylate 
• 176966-78-2 tert-butyl (5S)-5-(tert-butyldiphenylsilyloxy)-3,4-dehydro-piperidine-2-one-1-carboxylate 

Relevant articles and documents

Synthesis of homochiral piperidine derivatives from S-glutamic acid. Stereoselective 1,4-addition of organocuprates to a Δ3-piperidine-2-one. A paroxetine analogue

Enantiomerically pure S-5-hydroxy-2-piperidinone 4, readily available from S-glutamic acid, serves as a key intermediate for the synthesis of 3,4-trans substituted piperidine derivatives. The substituents in the 4-position are introduced via 1,4-conjugate

Asymmetric total synthesis of Tofacitinib

A novel stereoselective synthesis of Tofacitinib (CP-690,550), a Janus tyrosine kinase (JAK3) specific inhibitor, has been achieved starting from (5S)-5-hydroxypiperidin-2-one in 10 steps from 2 with a 9.5% overall yield. The potentiality of this synthetic route is the obtention of tert-butyl-(3S,4R)-3- hydroxy-4-methylpiperidine-1-carboxylate (6b) as a new chiral precursor involved in the synthesis of CP690,550, in a three-step reaction, without epimerizations, rather than the 5 or more steps used in described reactions to achieve this compound from analogues of 6b.