71461-30-8

Basic information

• Product Name: 2α-Formylpyrrolidine-1-carboxylic acid benzyl ester
• Synonyms: (2S)-1-(Benzyloxycarbonyl)pyrrolidine-2-carbaldehyde;(2S)-1-(Benzyloxycarbonyl)pyrrolidine-2α-carbaldehyde;(2S)-2-Formylpyrrolidine-1-carboxylic acid benzyl ester;(2S)-2α-Formyl-1-pyrrolidinecarboxylic acid benzyl ester;2α-Formylpyrrolidine-1-carboxylic acid benzyl ester;N-Benzyloxycarbonyl-L-prolinal;(2S)-N-Benzyloxycarbonyl-2-pyrrolidinecarboxaldehyde;(S)-Benzyl 2-formylpyrrolidine-1-carboxylate
• CAS NO: 71461-30-8
• Molecular Formula: C₁₃H₁₅NO₃
• Molecular Weight: 233.26
• Mol File: 71461-30-8.mol
• Article Data: 58

Chemical Properties

• Appearance: /
• Density: 1.263
• CAS DataBase Reference: 2α-Formylpyrrolidine-1-carboxylic acid benzyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 2α-Formylpyrrolidine-1-carboxylic acid benzyl ester(71461-30-8)
• EPA Substance Registry System: 2α-Formylpyrrolidine-1-carboxylic acid benzyl ester(71461-30-8)

Safety Data

• Hazardous Substances Data: 71461-30-8(Hazardous Substances Data)

Usage

General Description

2α-Formylpyrrolidine-1-carboxylic acid benzyl ester, also known as benzyl L-pyroglutamate, is a chemical compound that belongs to the class of pyrrolidine carboxylic acid derivatives. It is commonly used in the synthesis of pharmaceuticals and other organic compounds. 2α-Formylpyrrolidine-1-carboxylic acid benzyl ester has a unique structure, with a pyrrolidine ring and a formyl group attached to the α position, as well as a benzyl ester group. It is often utilized as a building block in the creation of various drugs and biologically active molecules due to its versatile reactivity and functional group compatibility. Additionally, benzyl L-pyroglutamate has shown potential as an antiviral and antibacterial agent, making it of interest for further research and development in the field of medicinal chemistry.

Upstream product

• 51207-69-3 1,2-pyrrolidinedicarboxylic acid 2-ethyl 1-(phenylmethyl) ester 
• 501-53-1 benzyl chloroformate 
• 200499-57-6 (2R,4'S)-N-Benzyloxycarbonyl-2-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)pyrrolidine 
• 200499-52-1 (R)-4-Azido-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-butyric acid methyl ester 
• 200499-54-3 (R)-4-Azido-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-butyraldehyde 
• 200499-55-4 (R)-2-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]pyrrolidine 
• 136963-32-1 methyl 2,3-dideoxy-5,6-O-isopropylidene-4-O-p-tolylsulfonyl-D-erythro-hexonate 
• 68832-13-3 D-prolinol 
• 200499-58-7 (R)-1-benzyloxycarbonyl-2-[(S)-1,2-dihydroxyethyl]pyrrolidine 
• 182210-00-0 methyl (2R)-(benzyloxycarbonyl)pyrrolidine-2-carboxylate 
• 72597-18-3 (2R)-(+)-phenylmethyl 2-(hydroxymethyl)pyrrolidine-1-carboxylate 
• 61350-60-5 (S)-benzyloxycarbonyl-proline acid chloride 
• 200499-64-5 (2S,4'S)-N-Benzyloxycarbonyl-2-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)pyrrolidine 
• 200499-59-8 (S)-4-Azido-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-butyric acid methyl ester 

Downstream Products

• 154659-23-1 (2S)-1-(benzyloxycarbonyl)-2-<(1R,2R)-1,2-dihydroxy-4-phenylbutyl>pyrrolidine 
• 108142-90-1 tert-butyl (βS, 2S)-1-(benzyloxycarbonyl)-2-pyrrolidinehydracrylate 
• 141045-64-9 (2S,1'S,2'S)-N-(Benzyloxycarbonyl)-2-<1'-hydroxy-2'-(phenylthio)-3'-butenyl>pyrrolidine 
• 141116-76-9 (2S,1'R,2'R)-N-(Benzyloxycarbonyl)-2-<1'-hydroxy-2'-(phenylthio)-3'-butenyl>pyrrolidine 
• 138802-18-3 (S)-2-[(1R,2R)-1-Hydroxy-2-methyl-3-((4R,5S)-4-methyl-2-oxo-5-phenyl-oxazolidin-3-yl)-3-oxo-propyl]-pyrrolidine-1-carboxylic acid benzyl ester 
• 108807-54-1 Z-L-prolinal semicarbazone 
• 108807-54-1 Z-D-prolinal semicarbazone 
• 6216-63-3 N-Cbz-Prolinol 
• 143771-07-7 benzyl (S)-2-(2-oxoethyl)pyrrolidine-1-carboxylate 
• 110562-22-6 (2-Amino-3-hydroxy-phenyl)-((S)-2-dimethoxymethyl-pyrrolidin-1-yl)-methanone 
• 110562-21-5 N-(-3-methoxy-2-aminobenzoyl)-L-prolinal dimethyl acetal 
• 110575-89-8 (2-Amino-3-benzyloxy-phenyl)-((S)-2-dimethoxymethyl-pyrrolidin-1-yl)-methanone 
• 110562-23-7 O-benzyltilivalline 
• 80279-24-9 tilivalline 

Relevant articles and documents

Synthesis of chiral branched allylamines through dual photoredox/nickel catalysis

Allylamines are versatile building blocks in the synthesis of various naturally occurring products and pharmaceuticals. In contrast to terminal allylamines, the methods of synthesis of their branched congeners with internal, stereodefined double bonds are less explored. This work describes a new approach for the preparation of allylaminesviacross-coupling of alkyl bromides with simple 3-bromoallylamines by merging the photoredox approach and Ni catalysis. The reaction proceeds under mild conditions, under blue light irradiation, and in the presence of an organic dye, 4CzIPN, as a photocatalyst. The scope of suitable reaction partners is broad, including alkyl bromides bearing reactive functionalities (e.g., esters, nitriles, aldehydes, ketones, epoxides) andN-protected allylamines, as well asN-allylated secondary and tertiary amines and heterocycles. The employment of non-racemic starting materials allows for rapid and easy construction of complex multifunctional allylamine derivatives without the loss of enantiomeric purity.

Efficient synthesis of methyl (S)-4-(1-methylpyrrolidin-2-YL)-3-oxobutanoate as the key intermediate for tropane alkaloid biosynthesis with optically acitve form

Methyl (S)-4-(1-methylpyrrolidin-2-yl)-3-oxobutanoate has been synthesized for enzymatic studies on cyclization enzymes during cocaine biosynthesis in Erythroxylum coca plants. During the present new synthesis, L-proline was first protected with Cbz group and reduced to chiral amino alcohol, which were then followed by Swern oxidation, Wittig reaction and decarboxylative condensation. At the last step, N-methylamino acid precursor was treated with 1,1'-carbonyldiimidazole followed by reacting with methyl potassium malonate to give the 3-oxobutanoate in 54% overall yield. This new strategy has proven to avoid obvious racemization of the L-proline chiral center during the synthesis. In addition, six of the eight synthesis steps were performed via GAP chemistry/technology without the use of column chromatography for purification.

Selective Aerobic Oxidation of Primary Alcohols to Aldehydes

The 2-azaadamantane- N -oxyl (AZADO)- and 9-azanoradamantane- N -oxyl (nor-AZADO)-catalyzed selective oxidation of primary alcohols to the corresponding aldehydes is described. The use of tert -butyl nitrite as the co-catalyst enables efficient aerobic oxidation in MeCN instead of previously reported AcOH; this is important for the selectivity of the reaction. The addition of a solution of saturated aqueous NaHCO 3 after the completion of the reaction was effective to suppress the overoxidation of the product to the corresponding carboxylic acid during the workup.