125347-83-3

Basic information

• Product Name: BOC-DL-PROLINE ETHYL ESTER
• Synonyms: PYRROLIDINE-1,2-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER 2-ETHYL ESTER;BOC-DL-PROLINE ETHYL ESTER;1-tert-butyl 2-ethyl pyrrolidine-1,2-dicarboxylate;(R)-1-tert-butyl 2-ethyl pyrrolidine-1,2-dicarboxylate;2-ethyl 1-Methyl pyrrolidine-1,2-dicarboxylate;Boc-DL-Pro-OEt
• CAS NO: 125347-83-3
• Molecular Formula: C12H21NO4
• Molecular Weight: 243.3
• Mol File: 125347-83-3.mol
• Article Data: 20

Chemical Properties

• Boiling Point: 305.592 °C at 760 mmHg
• Flash Point: 138.618 °C
• Appearance: /
• Density: 1.101 g/cm³
• Storage Temp.: 2-8°C
• PKA: -3.22±0.40(Predicted)
• CAS DataBase Reference: BOC-DL-PROLINE ETHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: BOC-DL-PROLINE ETHYL ESTER(125347-83-3)
• EPA Substance Registry System: BOC-DL-PROLINE ETHYL ESTER(125347-83-3)

Safety Data

• Hazardous Substances Data: 125347-83-3(Hazardous Substances Data)

Usage

General Description

BOC-DL-PROLINE ETHYL ESTER is a chemical compound commonly used in organic synthesis and peptide research. It is formed by the esterification of BOC-DL-PROLINE, a non-essential amino acid, with ethanol. BOC-DL-PROLINE ETHYL ESTER is widely used as a protecting group in peptide synthesis, as it can be easily removed under mild acidic conditions. BOC-DL-PROLINE ETHYL ESTER is also used as a building block in the production of various pharmaceuticals and biologically active compounds. It is important in the field of medicinal chemistry and drug development as it can be utilized in the creation of diverse peptide-based drugs and therapeutic agents.

Upstream product

• 15761-39-4 1-(tert-butoxycarbonyl)-L-proline 
• 75-03-6 ethyl iodide 
• 147-85-3 L-proline 
• 24424-99-5 di-tert-butyl dicarbonate 
• 5817-26-5 ethyl (2S)-pyrrolidine-2-carboxylate 
• 60169-67-7 ethyl pyrrolidine-2-carboxylate 
• 89896-39-9 ethyl 5-azidovalerate 
• 144978-12-1 1-tert-butyl 2-ethyl (2R)-5-oxopyrrolidine-1,2-dicarboxylate 
• 33305-75-8 L-proline ethyl ester monohydrochloride 
• 194594-23-5 5-hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester 
• 575452-53-8 (+)-ethyl (3R,6S)-6-[(R)-1-phenylbutoxy]-1,2-oxazinane-3-carboxylate 
• 575452-52-7 (+)-ethyl (6S)-6-[(R)-1-phenylbutoxy]-5,6-dihydro-4H-1,2-oxazine-3-carboxylate 
• 73472-94-3 ethyl 3-bromo-2-(hydroxyimino)propanoate 
• 14660-52-7 ethyl 5-bromovalerate 

Downstream Products

• 1621435-37-7 tert-butyl 2-(((2S,3R)-1,3-bis(benzyloxy)-1-oxobutan-2-yl)carbamoyl)-2-(1-hydroxyethyl)pyrrolidine-1-carboxylate 
• 1621435-38-8 tert-butyl 2-((2S,3R)-1,3-bis(benzyloxy)-1-oxobutan-2-yl)-1-methyl-3-oxo-2,5-diazaspiro[3.4]octane-5-carboxylate 
• 1621435-94-6 tert-butyl 2-((2S,3R)-1-amino-3-hydroxy-1-oxobutan-2-yl)-1-methyl-3-oxo-2,5-diazaspiro[3.4]octane-5-carboxylate 
• 1621436-01-8 tert-butyl 2-(((2S,3R)-3-(benzyloxy)-1-oxo-1-(pyrrolidin-1-yl)butan-2-yl)carbamoyl)-2-(1-hydroxyethyl)pyrrolidine-1-carboxylate 
• 1621436-02-9 tert-butyl 2-((2S,3R)-3-(benzyloxy)-1-oxo-1-(pyrrolidin-1-yl)butan-2-yl)-1-methyl-3-oxo-2.5-diazaspiro[3.4]octane-5-carboxylate 
• 173690-69-2 tert-butyl 2-(2-cyanoacetyl)pyrrolidine-1-carboxylate 
• 1621482-38-9 1-tert-butyl 2-ethyl 2-((benzyloxy)methyl)pyrrolidine-1,2-dicarboxylate 
• 1194030-71-1 2-((benzyloxy)methyl)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid 
• 1621435-28-6 tert-butyl 2-((2S, 3R)-1, 3-bis (benzyloxy)-1-oxobutan-2-yl)-1-oxo-2, 5-diazaspiro [3.4] octane-5-carboxylate 
• 1621435-13-9 tert-butyl 2-(((2S, 3R)-1, 3-bis (benzyloxy)-1-oxobutan-2-yl) carbamoyl)-2-(hydroxymethyl) pyrrolidine-1-carboxylate 

Relevant articles and documents

Highly Chemoselective Reduction of N-Boc Protected Lactams

N-Boc protected lactams can be reduced chemoselectively in the presence of other groups such as esters, nitriles carbamates or double bonds by first reducing the amide carbonyl group into the corresponding hemiaminal using lithium triethylborohydride foll

Practical synthesis of ethyl 3-fluoro-1-pyrrole-2-carboxylate: A key fragment of a potent drug candidate against hepatitis b virus

We report herein the development of two efficient synthetic routes for the preparation of a key fragment required for the synthesis of potent drug candidates of Hepatitis B virus. The ethyl 3-fluoro-1-H-pyrrole-2-carboxylate scaffold was synthesized from readily available starting materials in good overall yields. The scalability of one of the developed routes was demonstrated and afforded the desired target in good yield and excellent purity (99%).

A (1 R, 3 S) -3 - amino-cyclopentanol hydrochloride preparation method (by machine translation)

The invention discloses a (1 R, 3 S) - 3 - amino-cyclopentanol hydrochloride of the preparation method, the method using chiral carboxylic acid with hydroxylamine to form the amide as chiral source, in copper catalyzed oxidation in the reaction system to rapidly obtain a chiral Diels - alder reaction product, after passes through the reduction reaction and alkaline deprotection reaction, and acidified after reaction to obtain the target product. Chiral inducing reagent chiral carboxylic acid by simple acidification, extraction processing can be reclaimed and reused. This kind of (1 R, 3 S) - 3 - amino-cyclopentanol hydrochloride preparation method has high operation safety and high selectivity, raw materials are easy, and the cost is low, the reaction time is short and simple process flow and the like. (by machine translation)

N-Heterocyclic Carbene Iron(III) Porphyrin-Catalyzed Intramolecular C(sp3)–H Amination of Alkyl Azides

Metal-catalyzed intramolecular C?H amination of alkyl azides constitutes an appealing approach to alicyclic amines; challenges remain in broadening substrate scope, enhancing regioselectivity, and applying the method to natural product synthesis. Herein we report an iron(III) porphyrin bearing axial N-heterocyclic carbene ligands which catalyzes the intramolecular C(sp3)–H amination of a wide variety of alkyl azides under microwave-assisted and thermal conditions, resulting in selective amination of tertiary, benzylic, allylic, secondary, and primary C?H bonds with up to 95 % yield. 14 out of 17 substrates were cyclized selectively at C4 to give pyrrolidines. The regioselectivity at C4 or C5 could be tuned by modifying the reactivity of the C5–H bond. Mechanistic studies revealed a concerted or a fast re-bound mechanism for the amination reaction. The reaction has been applied to the syntheses of tropane, nicotine, cis-octahydroindole, and leelamine derivatives.