190967-63-6

Basic information

• Product Name: benzyl (2S)-2-(2-hydroxyethyl)piperidine-1-carboxylate
• Synonyms: benzyl (2S)-2-(2-hydroxyethyl)piperidine-1-carboxylate
• CAS NO: 190967-63-6
• Molecular Weight: 263.337
• Mol File: 190967-63-6.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: benzyl (2S)-2-(2-hydroxyethyl)piperidine-1-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: benzyl (2S)-2-(2-hydroxyethyl)piperidine-1-carboxylate(190967-63-6)
• EPA Substance Registry System: benzyl (2S)-2-(2-hydroxyethyl)piperidine-1-carboxylate(190967-63-6)

Safety Data

• Hazardous Substances Data: 190967-63-6(Hazardous Substances Data)

Upstream product

• 13139-17-8 N-(Benzyloxycarbonyloxy)succinimide 
• 103639-57-2 (2S)-2-(2-methoxyethyl)piperidine 
• 3105-95-1 pipecolinic acid 
• 41373-39-1 (S)-pipecolinol 
• 1446128-19-3 benzyl (2S)-2-[(E)-2-nitrovinyl]piperidine-1-carboxylate 
• 212557-00-1 (S)-2-hydroxymethyl-piperidine-1-carboxylic acid benzyl ester 
• 212556-95-1 (S)-N-(benzyloxycarbonyl)-2-formylpiperidine 
• 501-53-1 benzyl chloroformate 
• 1000806-52-9 (E)-(7-benzyloxycarbonylamino)-2-heptenal 

Downstream Products

• 190846-25-4 N-benzyloxycarbonyl-2(S)-[2-(N-t-butoxycarbonyl-4-piperidyloxy)ethyl]piperidine 
• 190846-29-8 N-benzyloxycarbonyl-2(S)-{2-[N-(N,N'-di-t-butoxycarbonylamidino)-4-piperidyloxy]ethyl}piperidine 
• 441772-00-5 N-(N-benzyl-O-t-butyl-(S)-α-aspartyl)-2(S)-{2-[N-(N,N'-di-t-butoxycarbonylamidino)-4-piperidyloxy]ethyl}piperidine 
• 190846-55-0 N-(N-cyclohexyl-N-methyl-O-t-butyl-(S)-α-aspartyl)-2(S)-{2-[N-(N,N'-di-t-butoxycarbonylamidino)-4-piperidyloxy]ethyl}piperidine 
• 190846-41-4 N-(N-cyclohexyl-O-t-butyl-(S)-α-aspartyl)-2(S)-{2-[N-(N,N'-di-t-butoxycarbonylamidino)-4-piperidyloxy]ethyl}piperidine 
• 441772-05-0 N-(N-cyclohexyl-O-t-butyl-(S)-α-glutamyl)-2(S)-{2-[N-(N,N'-di-t-butoxycarbonylamidino)-4-piperidyloxy]ethyl}piperidine 
• 441772-06-1 N-(N-cyclohexyl-N-methyl-O-t-butyl-(S)-α-glutamyl)-2(S)-{2-[N-(N,N'-di-t-butoxycarbonylamidino)-4-piperidyloxy]ethyl}piperidine 
• 199942-74-0 (S)-2-(2-hydroxy-ethyl)-piperidine-1-carboxylic acid tert-butyl ester 
• 1374007-15-4 C₂₁H₃₅NO₃Si 
• 1374007-16-5 C₁₉H₃₄N₂O₃SSi 
• 1393456-04-6 C₁₉H₃₂N₂O₅SSi 
• 1393456-05-7 C₁₉H₂₁F₃N₄O₄S 
• 1374006-94-6 (S)-N-(4-((2-(2-hydroxyethyl)piperidin-1-yl)sulfonyl)phenyl)-1-methyl-3-(trifluoromethyl)-1H-pyrazole-5-carboxamide 
• 1374006-96-8 (S)-1-methyl-N-(4-((2-(2-morpholinoethyl)piperidin-1-yl)sulfonyl)phenyl)-3-(trifluoromethyl)-1H-pyrazole-5-carboxamide 

Relevant articles and documents

Henry-Nef reaction: A practical and versatile chiral pool route to 2-substituted pyrrolidine and piperidine alkaloids

The paper describes the synergistic protocol developed by combinatorial Henry and Nef reaction for the synthesis of 2-substituted pyrrolidine and piperidine alkaloids containing 1,3-aminoketone and 1,3-amino alcohol units. The utility of the protocol is demonstrated by asymmetric synthesis of 12 natural products of which asymmetric synthesis of (-)-N-methylpelletierine is presented for the first time. The one-carbon homologation described also provides an alternate route for the synthesis of key intermediates homoprolinol and homopipecolinol used as synthetic precursors for several alkaloids and construction of β-amino acids from α-amino acids.

Enantioselective Synthesis of (+)-α-Conhydrine and (-)-Sedamine by L-ProlineCatalysed α-Aminooxylation

An efficient organocatalytic approach to the enantioslective synthesis of two important piperidine alkaloids, namely (+)α-conhydrine (98% ee) and (-)-sedamine (95 % ee), by L-pro-line-catalysed α-aminooxylation of aldehydes has been developed. The strategy involves an intramolecular cyclization to construct the piperidine core.

Enantioselective organocatalytic intramolecular aza-Michael reaction: A concise synthesis of (+)-sedamine, (+)-allosedamine, and (+)-coniine

(Chemical Equation Presented) The intramolecular aza-Michael reaction of carbamates bearing remote α,β-unsaturated aldehydes under organocatalytic conditions took place with good yields and excellent ee's when Jorgensen catalyst IV was used in the process, giving rise to the enantioselective formation of several five- and six-membered heterocycles. The developed methodology was applied to the synthesis of three piperidine alkaloids.