357608-32-3

Basic information

• Product Name: (+)-tert-butyl (3R,4R)-3-hydroxy-4-phenylpiperidine-1-carboxylate
• Synonyms: (+)-tert-butyl (3R,4R)-3-hydroxy-4-phenylpiperidine-1-carboxylate
• CAS NO: 357608-32-3
• Molecular Weight: 277.364
• Mol File: 357608-32-3.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (+)-tert-butyl (3R,4R)-3-hydroxy-4-phenylpiperidine-1-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-tert-butyl (3R,4R)-3-hydroxy-4-phenylpiperidine-1-carboxylate(357608-32-3)
• EPA Substance Registry System: (+)-tert-butyl (3R,4R)-3-hydroxy-4-phenylpiperidine-1-carboxylate(357608-32-3)

Safety Data

• Hazardous Substances Data: 357608-32-3(Hazardous Substances Data)

Upstream product

• 357608-31-2 tert-butyl 3,4-dihydroxy-4-phenyl-piperidine-1-carboxylate 
• 186347-72-8 4-phenyl-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester 
• 138647-49-1 4-Trifluoromethanesulfonyloxy-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester 
• 79099-07-3 N-tert-butyloxycarbonylpiperidin-4-one 
• 24424-99-5 di-tert-butyl dicarbonate 
• 43064-12-6 1,2,3,6-tetrahydro-4-phenylpyridine hydrochloride 

Downstream Products

• 357608-33-4 (R,R)-tert-butyl 3-(4-bromo-benzyloxy)-4-phenyl-piperidine-1-carboxylate 

Relevant articles and documents

Highly enantioselective organocatalytic oxidative kinetic resolution of secondary alcohols using chiral alkoxyamines as precatalysts: Catalyst structure, active species, and substrate scope

The development and characterization of enantioselective organocatalytic oxidative kinetic resolution (OKR) of racemic secondary alcohols using chiral alkoxyamines as precatalysts are described. A number of chiral alkoxyamines have been synthesized, and their structure-enantioselectivity correlation study in OKR has led us to identify a promising precatalyst, namely, 7-benzyl-3-n-butyl-4-oxa-5-azahomoadamantane, which affords various chiral aliphatic secondary alcohols (ee up to >99%, krel up to 296). In a mechanistic study, chlorine-containing oxoammonium species were identified as the active species generated in situ from the alkoxyamine precatalyst, and it was revealed that the chlorine atom is crucial for high reactivity and enantioselectivity. The present OKR is the first successful example applicable to various unactivated aliphatic secondary alcohols, including heterocyclic alcohols with high enantioselectivity, the synthetic application of which is demonstrated by the synthesis of a bioactive compound.

Solid-phase synthesis of aspartic peptidase inhibitors: 3-alkoxy-4-aryl piperidines.

[reaction: see text]. The 3-alkoxy-4-aryl piperidines are non-peptide peptidomimetic inhibitors of several aspartic peptidases. The solid-phase functionalization of 3,4-disubstituted piperidine scaffolds using a traceless linker strategy is described. Syn