562817-60-1Relevant articles and documents
Synthesis of 2-Arylpiperidines via pd-catalyzed arylation of aza-Achmatowicz rearrangement products with arylboronic acids
Zhao, Guodong,Canterbury, Daniel P.,Taylor, Alexandria P.,Cheng, Xiayun,Mikochik, Peter,Bagley, Scott W.,Tong, Rongbiao
supporting information, p. 458 - 463 (2020/01/21)
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
Liu, Yi-Wen,Mao, Zhuo-Ya,Ma, Rui-Jun,Yan, Jia-Hang,Si, Chang-Mei,Wei, Bang-Guo
, p. 2100 - 2108 (2017/03/17)
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).
A Concise Enantioselective Synthesis of (+)-L-733,060 and (+)-T-2328 via Sequential Proline Catalysis
Lalwani, Komal G.,Sudalai, Arumugam
, p. 1339 - 1343 (2016/06/01)
A new, sequential proline-catalyzed approach to the synthesis of (+)-L-733,060 and (+)-T-2328 in high optical purity (93% ee) is described starting from phenyl N-Boc imine. The strategy involves proline-catalyzed Mannich reaction of an arylimine with acet
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
Devalankar, Dattatray A.,Chouthaiwale, Pandurang V.,Sudalai, Arumugam
supporting information, p. 102 - 104 (2014/01/06)
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
Efficient, stereodivergent access to 3-piperidinols by traceless P(OEt)3 cyclodehydration
Huy, Peter H.,Koskinen, Ari M. P.
supporting information, p. 5178 - 5181 (2013/11/06)
A stereodivergent and highly diastereoselective (dr up to >19:1 for both isomers), step economic (5-6 steps), and scalable synthesis (up to 14 g) of cis- and trans-2-substituted 3-piperidinols, the core motif of numerous bioactive compounds, providing efficient access to the NK-1 inhibitor L-733,060 is presented. Additionally, a "traceless" (referring to the simplified byproduct separation) cyclodehydration realizing simple P(OEt)3 as a substitute for PPh3 is developed.
Synthesis of (+)-L-733,060, (+)-CP-99,994 and (2S,3R)-3-hydroxypipecolic acid: Application of an organocatalytic direct vinylogous aldol reaction
Pansare, Sunil V.,Paul, Eldho K.
experimental part, p. 2119 - 2125 (2012/04/17)
The γ-butenolide obtained from an organocatalyzed, direct vinylogous aldol reaction of γ-crotonolactone and benzaldehyde serves as the key starting material in the expedient synthesis of a 3-hydroxy-2-phenyl piperidine intermediate which is converted to the target 2,3-disubstituted piperidines.
Enantioselective synthesis of (+)- l -733,060 and (+)-CP-99,994: Application of an ireland-claisen rearrangement/michael addition domino sequence
Garrido, Narciso M.,García, Mercedes,Sánchez, M. Rosa,Díez, David,Urones, Julio G.
scheme or table, p. 387 - 390 (2010/04/05)
An efficient asymmetric synthesis of (+)-l-733,060, (-)-(2S,3R)-1 and (+)-CP-99,994, starting from a Baylis-Hillman adduct, is described. The key steps include a novel domino reaction: stereoselective Ireland-Claisen rearrangement, asymmetric Michael addi
A stereoselective synthesis of (+)-L-733,060 from ethyl (R)-(+)-2,3-epoxypropanoate
Prevost, Sebastien,Phansavath, Phannarath,Haddad, Mansour
experimental part, p. 16 - 20 (2010/04/26)
An asymmetric synthesis of neurokinin substance P receptor antagonist (+)-L-733,060 starting from enantiomerically pure ethyl (R)-(+)-2,3-epoxypropanoate (ethyl glycidate) is described. The synthesis relies on a diastereoselective reductive amination, regioselective intramolecular epoxide opening, and in situ cyclization as the key steps.
A short enantioselective synthesis of (+)-L-733,060 via Shi epoxidation of a homoallylic carboxylate
Emmanuvel, Lourdusamy,Sudalai, Arumugam
, p. 5736 - 5738 (2008/12/22)
A short and efficient enantioselective synthesis of (+)-L-733,060 in 92% ee via Shi epoxidation of a homoallylic carboxylate is described. Johnson-Claisen rearrangement was employed to obtain the required carbon backbone, whilst intramolecular reductive O-to-N-ring expansion of a δ-azidolactone was used in the construction of the piperidine moiety.
Concise asymmetric synthesis of (+)-CP-99,994 and (+)-l-733,060 via efficient construction of homochiral syn-1,2-diamines and syn-1,2-amino alcohols
Liu, Run-Hua,Fang, Kai,Wang, Bing,Xu, Ming-Hua,Lin, Guo-Qiang
, p. 3307 - 3310 (2008/09/20)
(Chemical Equation Presented) An efficient asymmetric synthesis of human NK-1 SP receptor antagonists (+)-CP-99,994 and (+)-L-733,060 was achieved starting from a common chiral intermediate (5). Our route featured the SmI 2-induced reductive co
