174699-11-7

Basic information

• Product Name: ETHYL (S)-1-CBZ-NIPECOTATE
• Synonyms: ETHYL (S)-1-CBZ-NIPECOTATE ;(S)-1-Benzyl 3-ethyl piperidine-1,3-dicarboxylate;(S)-1,3-Piperidinedicarboxylic acid 3-ethyl 1-(phenylmethyl) ester
• CAS NO: 174699-11-7
• Molecular Formula: C₁₆H₂₁NO₄
• Molecular Weight: 291.34224
• Mol File: 174699-11-7.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 403.7°Cat760mmHg
• Flash Point: 198°C
• Appearance: /
• Density: 1.165g/cm³
• Vapor Pressure: 9.97E-07mmHg at 25°C
• Refractive Index: 1.533
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: ETHYL (S)-1-CBZ-NIPECOTATE(CAS DataBase Reference)
• NIST Chemistry Reference: ETHYL (S)-1-CBZ-NIPECOTATE(174699-11-7)
• EPA Substance Registry System: ETHYL (S)-1-CBZ-NIPECOTATE(174699-11-7)

Safety Data

• Hazardous Substances Data: 174699-11-7(Hazardous Substances Data)

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

• 3335-05-5 ethyl 1,4,5,6-tetrahydropyridine-3-carboxylate 
• 501-53-1 benzyl chloroformate 
• 71962-74-8 Ethyl nipecotate 
• 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 
• 917112-56-2 5,6-dihydro-4H-pyridine-1,3-dicarboxylic acid 1-benzyl ester 3-ethyl ester 
• 64-17-5 ethanol 
• 88466-74-4 (3S)-1-phenylmethoxycarbonylpiperidine-3-carboxylic acid 
• 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 
• 614-18-6 3-pyridinecarboxylic acid ethyl ester 

Downstream Products

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

Relevant articles and documents

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.

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.