166410-05-5

Basic information

• Product Name: BOC-4-OXO-L-PROLINE TERT-BUTYL ESTER
• Synonyms: BOC-4-OXO-L-PROLINE TERT-BUTYL ESTER;N-T-BOC-4-OXO-L-PROLINE TERT-BUTYL ESTER;N-BOC-4-OXO-L-PROLINE TERT-BUTYL ESTER;1,2-di-tert-butyl (2S)-4-oxopyrrolidine-1,2- dicarboxylate;(2S) tert-butyl N-(tert-butoxycabonyl)-4-oxoprolinate;Boc-4-OXO-Pro-OtBu;(2S)-1,2-Bis(tert-butoxycarbonyl)-4-oxopyrrolidine, 4-Oxo-L-proline tert-butyl ester, N-BOC protected;Bis(tert-butyl) (2S)-4-oxopyrrolidine-1,2-dicarboxylate
• CAS NO: 166410-05-5
• Molecular Formula: C₁₄H₂₃NO₅
• Molecular Weight: 285.34
• Mol File: 166410-05-5.mol
• Article Data: 9

Chemical Properties

• Melting Point: 64-67°C
• Boiling Point: 366.7 ºC at 760 mmHg
• Flash Point: 175.6 ºC
• Appearance: /
• Density: 1.138 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.516
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• PKA: -3.86±0.40(Predicted)
• CAS DataBase Reference: BOC-4-OXO-L-PROLINE TERT-BUTYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: BOC-4-OXO-L-PROLINE TERT-BUTYL ESTER(166410-05-5)
• EPA Substance Registry System: BOC-4-OXO-L-PROLINE TERT-BUTYL ESTER(166410-05-5)

Safety Data

• Hazardous Substances Data: 166410-05-5(Hazardous Substances Data)

Usage

General Description

BOC-4-OXO-L-PROLINE TERT-BUTYL ESTER is a chemical compound that is a derivative of proline, an amino acid. It is a compound with a tert-butyl ester group, which provides stability and protection to the proline moiety. BOC-4-OXO-L-PROLINE TERT-BUTYL ESTER is commonly used in organic synthesis as a building block for the production of pharmaceuticals, agrochemicals, and other fine chemicals. Its stable nature and versatility make it a valuable reagent in the synthesis of various complex molecules.

InChI:InChI=1/C10H15NO5/c1-10(2,3)16-9(15)11-5-6(12)4-7(11)8(13)14/h7H,4-5H2,1-3H3,(H,13,14)/t7-/m0/s1

Upstream product

• 13726-69-7 (2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid 
• 7529-22-8 4-methylmorpholine N-oxide 
• 1634-04-4 tert-butyl methyl ether 
• 84348-37-8 N-tert-butoxycarbonyl-4-oxo-L-proline 
• 51-35-4 4R-4-hydroxyproline 
• 24424-99-5 di-tert-butyl dicarbonate 
• 170850-75-6 BOC-Hyp-OtBu 
• 75-65-0 tert-butyl alcohol 

Downstream Products

• 344286-68-6 tert-butyl N^α-Boc-cis-4-hydroxy-4-phenyl-L-prolinate 
• 1201986-55-1 ((R)-3-(4-fluorophenyl)pyrrolidin-1-yl)((2S,4R)-4-(fluorophenyl)pyrrolidin-2-yl)methanone hydrochloride 
• 1201987-30-5 (2S,4R)-tert-butyl 4-(4-fluorophenyl)-2-((R)-3-(4-fluorophenyl)pyrrolidine-1-carbonyl)pyrrolidine-1-carboxylate 
• 1201986-76-6 (2S,4R)-1-(tert-butoxycarbonyl)-4-(4-fluorophenyl)-pyrrolidine-2-carboxylic acid 
• 1201986-75-5 (2S,4R)-4-(4-fluorophenyl)-pyrrolidine-2-carboxylic acid 
• 1201986-74-4 (S)-4-(4-fluorophenyl)-2,5-dihydro-1H-pyrrole-2-carboxylic acid 
• 1535212-06-6 C₃₁H₄₀F₂N₄O₇ 
• 860781-14-2 tert-butyl (2S,3S,4S)-[3-²H₁]-N-tert-butoxycarbonyl-4-O-para-toluenesulfonyloxyprolinate 
• 860781-13-1 tert-butyl (2S,3R,4S)-[3-²H₁]-N-tert-butoxycarbonyl-4-O-para-toluenesulfonyloxyprolinate 
• 860781-15-3 tert-butyl (2S,4S)-[3,3-²H₂]-N-tert-butoxycarbonyl-4-O-para-toluenesulfonyloxyprolinate 

Relevant articles and documents

Stereoselective synthesis of (3S,4S)-tert-butyl-N-Boc-3-ethyl-4-hydroxy-l- prolinate and (3S,4R)-tert-butyl-N-Boc-3-ethyl-4-hydroxy-l-prolinate

Diastereomers of tert-butyl-N-Boc-3-ethyl-4-hydroxy-l-prolinate 1 and 2 have been synthesized in six steps starting from readily available Boc-protected trans-4-hydroxy-l-proline. The key reactions in the synthesis are asymmetric reductions, firstly on th

Synthesis of 4-(Arylmethyl)proline Derivatives

A synthesis of 4 - (arylmethyl)proline by using Suzuki cross-couplings was developed. The route permits access to a variety of 4-substituted proline derivatives bearing various aryl moieties that expand the toolbox of proline analogues for studies in chemistry and biology.

An Unconventional Redox Cross Claisen Condensation-Aromatization of 4-Hydroxyprolines with Ketones

Reaction of α-amino acids, particularly prolines and their derivatives with carbonyl compounds via decarboxylative redox process, is a viable strategy for synthesis of structurally diverse nitrogen centered heterocyclics. In these processes, the decarboxylation is the essential driving force for the processes. The realization of the redox process without decarboxylation may offer an opportunity to explore new reactions. Herein, we report the discovery of an unprecedented redox Claisen-type condensation aromatization cascade reaction of 4-substituted 4-hydroxyproline and its esters with unreactive ketones. We found that the use of propionic acid as a catalyst and a co-solvent can change the reaction course. The commonly observed redox decarboxylation and aldol condensation reactions are significantly minimized. Moreover, unreactive ketones can effectively participate in the Claisen condensation reaction. The new reactivity enables a redox cyclization via an unconventional Claisen-type condensation reaction of in situ formed enamine intermediates from ketone precursors with 4-substituted 4-hydroxyproline and its esters as electrophilic acylation partners. Under the reaction conditions, the cascade process proceeds highly regio- and stereoselectively to afford highly synthetically and biologically valued cis-2,3-dihydro-1H-pyrrolizin-1-ones with a broad substrate scope in efficient 'one-pot' operation, whereas such structures generally require multiple steps.