142764-69-0

Basic information

• Product Name: 1(2H)-Pyridinecarboxylic acid, 3,4-dihydro-4-oxo-2-propyl-, phenylmethyl ester, (S)-
• CAS NO: 142764-69-0
• Molecular Formula: C16H19NO3
• Molecular Weight: 273.332
• Mol File: 142764-69-0.mol

Chemical Properties

• CAS DataBase Reference: 1(2H)-Pyridinecarboxylic acid, 3,4-dihydro-4-oxo-2-propyl-, phenylmethyl ester, (S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1(2H)-Pyridinecarboxylic acid, 3,4-dihydro-4-oxo-2-propyl-, phenylmethyl ester, (S)-(142764-69-0)
• EPA Substance Registry System: 1(2H)-Pyridinecarboxylic acid, 3,4-dihydro-4-oxo-2-propyl-, phenylmethyl ester, (S)-(142764-69-0)

Safety Data

• Hazardous Substances Data: 142764-69-0(Hazardous Substances Data)

Upstream product

• 501-53-1 benzyl chloroformate 
• 213197-97-8 1,4-dihydro-1-(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)-pyridin-4(1H)-one 
• 126378-42-5 4-methoxy-3-(trisopropylsilyl)pyridine 
• 132599-74-7 (S)-3-Methyl-2-((S)-4-oxo-2-propyl-3,4-dihydro-2H-pyridin-1-yl)-pentanoic acid methyl ester 
• 626-64-2 pyridin-4-ol 
• 927-77-5 n-propylmagnesium bromide 
• 620-08-6 4-methoxypyridine 
• 628-91-1 di-n-propyl zinc 
• 132599-85-0 [(S)-2-Methyl-1-((S)-4-oxo-2-propyl-3,4-dihydro-2H-pyridin-1-yl)-butyl]-carbamic acid benzyl ester 
• 132599-74-7 N-<(S)-1-(methoxycarbonyl)-(S)-2-methylbutyl>-(6S)-2,3-didehydro-6-n-propylpiperidin-4-one 
• 132599-85-0 [(1S,2S)-2-Methyl-1-((S)-4-oxo-2-propyl-3,4-dihydro-2H-pyridin-1-yl)-butyl]-carbamic acid benzyl ester 
• 142764-67-8 N-<(S)-1-carboxy-(S)-2-methylbutyl>-(6S)-2,3-didehydro-6-n-propylpiperidin-4-one 
• 767321-62-0 (2S)-5-(phenylselenyl)-2-propyl-1-(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)piperidin-4-one 
• 121675-89-6 (2S)-N-(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)-2-n-propyl-5,6-didehydro-piperidin-4-one 

Downstream Products

• 767321-65-3 (2S,6R)-1-(benzyloxycarbonyl)-6-(3-chloropropyl)-2-propylpiperidin-4-one 
• 934016-33-8 benzyl (S)-2-propylpiperidine-1-carboxylate 
• 142780-95-8 N-(benzyloxycarbonyl)-(6S)-4-(1,3-dithiolan-4-yl)-6-n-propylpiperidine 
• 555-92-0 (S)-coniine hydrochloride 
• 142764-70-3 N-(benzyloxycarbonyl)-(6S)-6-n-propylpiperidin-4-one 

Relevant articles and documents

Highly Enantioselective Catalytic Addition of Grignard Reagents to N-Heterocyclic Acceptors

General methods to prepare chiral N-heterocyclic molecular scaffolds are greatly sought after because of their significance in medicinal chemistry. Described here is the first general catalytic methodology to access a wide variety of chiral 2- and 4-substituted tetrahydro-quinolones, dihydro-4-pyridones, and piperidones with excellent yields and enantioselectivities, utilizing a single catalyst system.

Catalytic enantioselective addition of dialkylzinc reagents to N-acylpyridinium salts

(Chemical equation presented) A pinch of salt: The first catalytic addition of dialkylzinc reagents to N-acylpyridinium salts with good yields and excellent enantioselectivities uses a copper-(S)-L complex as the catalyst. The versatility of the method is

Stereoselective synthesis of enantiomerically pure piperidine derivatives by N-galactosylation of pyridones

Stereoselective desymmetrization of 4-pyridone has been achieved through selective N-galactosylation, activation of the N-(galactosyl)pyridone by O-silylation and immediate addition of Grignard compounds. Chiral piperidine derivatives, e.g. (S)-(+)-coniine and (5S,9S)-(+)-indolozidine 167B, were synthesised in enantiomerically pure form using these highly regio- and stereoselective reactions. After N-galactosylation of 2-pyridone and O-silylation of the N-galactosyl-2-pyridone, addition of a Grignard compound proceeded with high 1,4-regioselectivity and complete diastereoselectivity, to furnish 4-substituted 5,6-dehydro-2-piperidones. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.

Asymmetric Tandem Mannich-Michael Reactions of Amino Acid Ester Imines with Danishefsky's Diene

Imines 1 derived from aromatic, aliphatic, and functionalized aldehydes and various amino acid esters react with Danishefsky's diene under Lewis acid catalysis via a tandem Mannich-Michael mechanism to give cyclic 6-substituted 2,3-didehydro-4-piperidinones in good to high yields and with diastereomeric ratios reaching from 92:8 up to 97:3.The chiral auxiliary is removed by conversion of the α C atom of the amino acid into an acetalic center, employing a Curtius reaction as the key step.For the elucidation of the absolute configuration, the alkaloids (S)-coniine and (R)-δ-coniceine are synthesized from the enaminones 5i and 5r.

Conversion of N-acyl-2,3-dihydro-4-pyridones to 4-chloro-1,2-dihydropyridines using the Vilsmeier reagent

N-Acyl-2,3-dihydro-4-pyridones are converted to 1-acyl-4-chloro-1,2-dihydropyridines in one step using one equivalent of Vilsmeier reagent. This conversion was utilized in an asymmetric synthesis of (-)-coniine.