81658-25-5

Basic information

• Product Name: tert-Butyl (2S)-2-(hydroxymethyl)-5-oxopyrrolidine-1-carboxylate
• Synonyms: tert-Butyl (2S)-2-(hydroxymethyl)-5-oxopyrrolidine-1-carboxylate;Boc-L-PyroglutaMinol;2-Methyl-2-propanyl (2S)-2-(hydroxyMethyl)-5-oxo-1-pyrrolidinecarboxylate;(S)-tert-Butyl 2-(hydroxymethyl)-5-oxopyrrolidine-1-carboxylate;1-Pyrrolidinecarboxylic acid,2-(hydroxymethyl)-5-oxo-,1,1-dimethylethyl ester,(2S)-;(S)-1-Boc-2-(hydroxymethyl)-5-oxopyrrolidine;Boc-L-Pyr-OL;Boc-Pyr-Ol
• CAS NO: 81658-25-5
• Molecular Formula: C₁₀H₁₇NO₄
• Molecular Weight: 215.247
• EINECS: 1592732-453-0
• Mol File: 81658-25-5.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 370.861 °C at 760 mmHg
• Flash Point: 178.09 °C
• Appearance: /
• Density: 1.182
• Storage Temp.: 2-8°C
• CAS DataBase Reference: tert-Butyl (2S)-2-(hydroxymethyl)-5-oxopyrrolidine-1-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: tert-Butyl (2S)-2-(hydroxymethyl)-5-oxopyrrolidine-1-carboxylate(81658-25-5)
• EPA Substance Registry System: tert-Butyl (2S)-2-(hydroxymethyl)-5-oxopyrrolidine-1-carboxylate(81658-25-5)

Safety Data

• Hazardous Substances Data: 81658-25-5(Hazardous Substances Data)

Usage

General Description

"Tert-Butyl (2S)-2-(hydroxymethyl)-5-oxopyrrolidine-1-carboxylate" is a chemical compound with the molecular formula C10H17NO4. tert-Butyl (2S)-2-(hydroxymethyl)-5-oxopyrrolidine-1-carboxylate is a derivative of pyrrolidine and contains a tert-butyl group, a hydroxymethyl group, and a carboxylate group. It is commonly used in organic synthesis and pharmaceutical research as a building block for the creation of various molecules and drugs. Additionally, it has potential applications in the development of new materials and biochemical studies.

Upstream product

• 56-86-0 L-glutamic acid 
• 141393-83-1 (4S,5S,6R)-N-(tert-butoxycarbonyl)-6,7-O-isopropylidene-2,3-dideoxy-hept-2-enono-1,4-lactam 
• 141293-14-3 N-(tert-butoxycarbonyl)pyrrol-2(5H)-one 
• 185303-86-0 N-(tert-butoxycarbonyl)-6,7-O-isopropylidene-2,3-dideoxy-L-arabinoheptono-1,4-lactam 
• 141393-87-5 4-<(tert-butoxycarbonyl)amino>-6,7-O-isopropylidene-2,3,4-trideoxy-L-arabino-hept-2-enonic acid 1,4-lactam 
• 141293-28-9 N-(tert-butoxycarbonyl)-2-[(tert-butyldimethylsilyl)oxy]pyrrole 
• 17342-08-4 (S)-Pyroglutaminol 
• 106191-02-0 (S)-5-((tert-butyldimethylsilyloxy)methyl)pyrrolidin-2-one 
• 132974-83-5 (5S)-5-[[(tert-butyldiphenylsilyl)oxy]methyl]pyrrolidin-2-one 
• 24424-99-5 di-tert-butyl dicarbonate 
• 138629-30-8 (S)-tert-butyl 2-((tert-butyldiphenylsilyloxy)methyl)-5-oxopyrrolidine-1-carboxylate 
• 81658-26-6 tert-butyl (S)-2-(((tert-butyldimethylsilyl)oxy)methyl)-5-oxopyrrolidin-1-carboxylate 
• 185303-87-1 tert-butyl (S)-2-formyl-5-oxopyrrolidine-1-carboxylate 
• 145221-04-1 (S)-1-(tert-butyloxycarbonyl)-5-(trityloxymethyl)-2-pyrrolidinone 

Downstream Products

• 81658-26-6 tert-butyl (S)-2-(((tert-butyldimethylsilyl)oxy)methyl)-5-oxopyrrolidin-1-carboxylate 
• 53100-44-0 L-N-t-butoxycarbonylpyroglutamic acid 
• 138629-30-8 (S)-tert-butyl 2-((tert-butyldiphenylsilyloxy)methyl)-5-oxopyrrolidine-1-carboxylate 
• 192389-43-8 (5S)-1-(benzyloxycarbonyl)-5-[(tert-butyldiphenylsilyl)oxymethyl]-2-hydroxypyrrolidine 
• 181705-71-5 (5S,2'S,5'S)-5-[5'-(tert-butyldiphenylsilyloxymethyl)pyrrolidin-2'yl]-tetrahydrofuran-2-one 
• 181705-72-6 (3S,8S,9R)-3-(tert-butyldiphenylsilanyloxymethyl)-8-hydroxyhexahydroindolizin-5-one 
• 181705-70-4 (5S,2'S,5'S)-5-[1'-(tert-butoxycarbonyl)-5'-(tert-butyldiphenylsilyloxymethyl)pyrrolidin-2'-yl]-2(5H)-furanone 
• 782496-03-1 (2S,5S)-N-(tert-butoxycarbonyl)-5[(tert-butyldiphenylsilyl)oxymethyl]-2-methoxypyrrolidine 
• 244274-71-3 (3S,6R,7R,8R,8aS)-3-(tert-butyldiphenylsilyloxymethyl)-6,7,8-trihydroxyindolizidin-5-one 
• 181705-84-0 2-(tert-butyl-diphenyl-silanyloxymethyl)-5-(5-oxo-tetrahydro-furan-2-yl)-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 244274-73-5 8-(tert-butyl-dimethyl-silanyloxy)-3-(tert-butyl-diphenyl-silanyloxymethyl)-octahydro-indolizine 
• 244274-69-9 (3S,8S,8aS)-3-(tert-butyldiphenylsilyloxymethyl)-8-(tert-butyldimethylsilyloxy)indolizidin-5-one 
• 244274-70-2 (3R,4R,5R,2'S,5'S)-5-[1'-(tert-butoxycarbonyl)-5'-(tert-butyldiphenylsilyloxymethyl)pyrrolidin-2'-yl]-3,4-dihydroxytetrahydrofuran-2-one 
• 244274-75-7 (3S,6S,7S,8R,8aS)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-6,7,8-tris-trimethylsilanyloxy-octahydro-indolizine 

Relevant articles and documents

Unprecedented migration of N-alkoxycarbonyl groups in protected pyroglutaminol.

[figure: see text] Cleavage of an O-silyl ether in an N-BOC-protected pyroglutaminol using TBAF led to an unprecedented migration of the BOC group. An investigation of the mechanism, based on experimental data and quantum mechanical calculations, is presented. Similar migration was observed for N-Cbz and N-methoxycarbonyl groups.

Expeditious syntheses of sugar-modified nucleosides and collections thereof exploiting furan-, pyrrole-, and thiophene-based siloxy dienes

A series of individual sugar-modified pyrimidine nucleosides including enantiomerically enriched 2',3'-dideoxynucleosides 14a-c (α and β anomers of L- and D-series), 2',3'-dideoxy-4'-thionucleosides 21a-c (α and β anomers of L- and D-series), and 2',3'-dideoxy-4'-azanucleosides 28a-c (β anomers of L- and D-series) were synthesized, with uniform chemistry and high stereochemical efficiency, exploiting a triad of versatile heterocyclic siloxy dienes, namely, 2-(tert-butyldimethylsiloxy)furan (TBSOF), 2-(tert- butyldimethylsiloxy)thiophene (TBSOT), and N-(tert-butoxycarbonyl)-2-(tert- butyldimethylsiloxy)pyrrole (TBSOP). The synthetic procedure advantageously used both enantiomers of glyceraldehyde acetonide (D-1 and L-1) as sources of chirality and as synthetic equivalents of the formyl cation. The outlined chemistry also allowed for the rapid assemblage of a 30-member collection of racemic nucleosides (D,L-L) as well as one 15-member ensemble of chiral analogues (L-L), along with some related sublibraries.

Synthesis of (3R,4R,5R)-1-(tert-butoxycarbonyl)-3,4-isopropylidenedioxy-5-methoxyme thyl-2-pyrrolidinone from (S)-pyroglutaminol

(3R,4R,5R)-1-(tert-Butoxycarbonyl)-3,4-isopropylidenedioxy-5-methoxyme thyl-2-pyrrolidinone (6), a useful chiral intermediate for the preparation of calyculins, was synthesized starting from (S)-pyroglutaminol via the O-methylation of 1c with diazomethane in the presence of fluoboric acid and cis-dihydroxylation of the α,β-unsaturated lactam (4) as the key reactions.