174699-11-7

Usage

Uses

Ethyl (S)-1-Cbz-nipecotate was prepared as a ligand for monoamine receptors and transporters.

InChI:InChI=1/C16H21NO4/c1-2-20-15(18)14-9-6-10-17(11-14)16(19)21-12-13-7-4-3-5-8-13/h3-5,7-8,14H,2,6,9-12H2,1H3/t14-/m0/s1

Upstream product

• 64-17-5 ethanol 
• 88466-74-4 (3S)-1-phenylmethoxycarbonylpiperidine-3-carboxylic acid 
• 917112-56-2 5,6-dihydro-4H-pyridine-1,3-dicarboxylic acid 1-benzyl ester 3-ethyl ester 
• 501-53-1 benzyl chloroformate 
• 71962-74-8 Ethyl nipecotate 
• 637337-59-8 (4R)-3-[(2S)-2-({[(benzyloxy)carbonyl]amino}methyl)-5-bromo-1-oxopentyl]-4-(1-methylethyl)-5,5-diphenyloxazolidin-2-one 
• 637337-43-0 (4R)-3-(5-bromo-1-oxopentyl)-4-(1-methylethyl)-5,5-diphenyloxazolidin-2-one 
• 4509-90-4 5-bromovaleroyl chloride 
• 868632-22-8 (4R)-3-({(3S)-1-[(benzyloxy)carbonyl]piperidin-3-yl}carbonyl)-4-(1-methylethyl)-5,5-diphenyloxazolidin-2-one 
• 3335-05-5 ethyl 1,4,5,6-tetrahydropyridine-3-carboxylate 
• 614-18-6 3-pyridinecarboxylic acid ethyl ester 

Downstream Products

• 1092074-85-5 C₁₆H₁₉NO₇ 
• 37675-18-6 (S)-(+)-nipecotic acid ethyl ester 

Relevant academic research and scientific papers

Manganese Catalyzed Hydrogenation of Enantiomerically Pure Esters

A manganese-catalyzed hydrogenation of esters has been accomplished with TONs up to 1000, using cheap, environmentally benign, potassium carbonate and simple alcohols as activator and solvent, respectively. The weakly basic conditions lead to good functional group tolerance and enable the hydrogenation of enantiomerically enriched α-chiral esters with essentially no loss of stereochemical integrity.

Asymmetric hydrogenation of pyridines: Enantioselective synthesis of nipecotic acid derivatives

An asymmetric hydrogenation process of 3-substituted pyridine derivatives has been developed with the use of a Rh-TangPhos complex as the catalyst. The whole process consists of an efficient partial hydrogenation of nicotinate and a subsequent highly enan

Preparation of β2-amino acid derivatives (β2hThr, β2hTrp, β2hMet, β2hPro, β2hLys, pyrrolidine-3-carboxylic acid) by using DIOZ as chiral auxiliary

The title compounds were prepared from valine-derived N-acylated oxazolidin-2-ones, 1-3, 7, 9, by highly diastereoselective (≥ 90%) Mannich reaction (→ 4-6; Scheme 1) or aldol addition (→ 8 and 10; Scheme 2) of the corresponding Ti- or B-enolates as the key step. The superiority of the '5,5-diphenyl-4-isopropyl-1,3-oxazolidin-2-one' (DIOZ) was demonstrated, once more, in these reactions and in subsequent transformations leading to various t-Bu-, Boc-, Fmoc-, and Cbz-protected β2-homoamino acid derivatives 11-23 (Schemes 3-6). The use of ω-bromo-acyl-oxazolidinones 1-3 as starting materials turned out to open access to a variety of enantiomerically pure trifunctional and cyclic carboxylic-acid derivatives.

Methods for the stereoselective synthesis of substituted piperidines

One aspect of the present invention relates to methods of synthesizing substituted piperidines. A second aspect of the present invention relates to stereoselective methods of synthesizing substituted piperidines. The methods of the present invention will