148700-84-9

Basic information

• Product Name: (2S,3S)-3-[3,5-Bis(trifluoromethyl)benzyloxy]-2-phenylpiperidine
• Synonyms: L-733060
• CAS NO: 148700-84-9
• Molecular Formula: C₂₀H₁₉F₆NO
• Molecular Weight: 403.37093
• Mol File: 148700-84-9.mol
• Article Data: 23

Chemical Properties

• CAS DataBase Reference: (2S,3S)-3-[3,5-Bis(trifluoromethyl)benzyloxy]-2-phenylpiperidine(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3S)-3-[3,5-Bis(trifluoromethyl)benzyloxy]-2-phenylpiperidine(148700-84-9)
• EPA Substance Registry System: (2S,3S)-3-[3,5-Bis(trifluoromethyl)benzyloxy]-2-phenylpiperidine(148700-84-9)

Safety Data

• Hazardous Substances Data: 148700-84-9(Hazardous Substances Data)

Upstream product

• 216769-41-4 (4S-trans)-4,5-dihydro-2,4-diphenyl-5-vinyloxazoline 
• 201047-53-2 (4S,5R)-2,4-Diphenyl-4,5-dihydro-oxazole-5-carbaldehyde 
• 691871-80-4 (4S,5S)-(2,5-dihydroxy-1-phenylpentyl)-carbamic acid tert-butyl ester 
• 323579-86-8 methyl (2R,3S)-3-(tert-butoxycarbonylamino)-2-(tert-butyldimethyl-silanyloxy)-3-phenylpropionate 
• 195624-97-6 (2R,3S)-3-acetylamino-2-hydroxy-3-phenylpropanoic acid isopropyl ester 
• 157240-36-3 (2R,3S)-3-phenylisoserine methyl ester 
• 124605-42-1 methyl (2R,3S)-3-(tert-butoxycarbonylamino)-2-hydroxy-3-phenylpropionate 
• 60512-85-8 (E)-isopropyl cinnamate 
• 140-10-3 (E)-3-phenylacrylic acid 
• 873914-62-6 (4S,5S)-5-tert-butoxycarbonylamino-4-(tert-butyldimethylsilanyloxy)-5-phenylpent-2-enoic acid ethyl ester 
• 873914-61-5 (2R,3S)-2-[(tert-butyldimethyl-silanyloxy)-3-hydroxy-1-phenylpropyl]-carbamic acid tert-butyl ester 
• 873914-63-7 (4S,5S)-5-(tert-butoxycarbonylamino)-4-hydroxy-5-phenylpentanoic acid ethyl ester 
• 654639-86-8 Benzoic acid (S)-1-((S)-tert-butoxycarbonylamino-phenyl-methyl)-allyl ester 
• 32247-96-4 3,5-bis(trifluoromethyl)benzyl bromide 

Downstream Products

• 159249-47-5 tert-butyl (2S,3S)-3-hydroxy-2-phenylpiperidine-1-carboxylate 
• 191669-62-2 (S)-tert-butyl 3-carbonyl-2-phenylpiperidine-1-carboxylic acid 

Relevant articles and documents

Synthesis of 2-Arylpiperidines via pd-catalyzed arylation of aza-Achmatowicz rearrangement products with arylboronic acids

The first Pd-catalyzed arylation of aza-Achmatowicz rearrangement products with arylboronic acids is achieved, providing versatile 2-Aryldihydropyridinones for facile synthesis of highly functionalized 2-Arylpiperidines. Key to this arylation is the use of non-phosphine-ligand palladium precatalyst. The substrate scope is demonstrated with >26 examples, and the utility of 2-Aryldihydropyridinones is illustrated by the synthesis of a small collection of 2-Arylpiperidines with substituents or functional groups at any carbon (C2-C6) as well as two NK1 receptor antagonists (+)-CP-999,94 and (+)-L-733,060.

Divergent syntheses of L-733, 060 and CP-122721 from functionalized pieridinones made by one-pot tandem cyclization

An efficient diastereoselective approach to access trans-5-hydroxy-6-substituted 2-piperidinones skeleton has been developed through one-pot intramolecular tandem process of O-benzyl protected aldimine 11 with Grignard reagents. The diastereoselectivity of substitution at C-6 position of 2-piperidinone was controlled by α-benzyloxy group. In addition, the utility of this straightforward cascade process is demonstrated by the asymmetric syntheses of (+)-L-733, 060 (2) and its 2-substituted analogue 3, as well as (+)-CP-122721 (5).

Concise enantioselective syntheses of (+)-L-733,060 and (2 S,3 S)-3-hydroxypipecolic acid by cobalt(III)(salen)-catalyzed two-stereocenter hydrolytic kinetic resolution of racemic azido epoxides

An efficient synthesis of the 2,3-disubstituted piperidines (+)-L-733,060 and (2S,3S)-3-hydroxypipecolic acid (≥99% ee) in high optical purity from commercially available starting materials is described. The strategy involves a cobalt-catalyzed hydrolytic