133007-27-9

Basic information

• Product Name: (3R-CIS)-(-)-3-PHENYLTETRAHYDROPYRROLO-[2,1-B]-OXAZOL-5(6H)-ONE
• Synonyms: (3R-CIS)-(-)-3-PHENYLTETRAHYDROPYRROLO-[2,1-B]-OXAZOL-5(6H)-ONE;(3R-cis)-(-)-3-Phenyltetrahydropyrrolo-[2,1-b]oxazol-5(6H)-one,97%
• CAS NO: 133007-27-9
• Molecular Formula: C₁₂H₁₃NO₂
• Molecular Weight: 203.24
• Mol File: 133007-27-9.mol

Chemical Properties

• Melting Point: 76-80 °C
• Boiling Point: 341.55°C (rough estimate)
• Flash Point: 185.6°C
• Appearance: /
• Density: 1.1255 (rough estimate)
• Vapor Pressure: 4.47E-06mmHg at 25°C
• Refractive Index: 1.5260 (estimate)
• CAS DataBase Reference: (3R-CIS)-(-)-3-PHENYLTETRAHYDROPYRROLO-[2,1-B]-OXAZOL-5(6H)-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: (3R-CIS)-(-)-3-PHENYLTETRAHYDROPYRROLO-[2,1-B]-OXAZOL-5(6H)-ONE(133007-27-9)
• EPA Substance Registry System: (3R-CIS)-(-)-3-PHENYLTETRAHYDROPYRROLO-[2,1-B]-OXAZOL-5(6H)-ONE(133007-27-9)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 36/37
• Hazardous Substances Data: 133007-27-9(Hazardous Substances Data)

Usage

Chemical Properties

off-white to light yellow crystalline powder

InChI:InChI=1/C12H13NO2/c14-11-6-7-12-13(11)10(8-15-12)9-4-2-1-3-5-9/h1-5,10,12H,6-8H2/t10-,12-/m0/s1

Upstream product

• 332-77-4 2,5-dihydro-2,5-dimethoxyfuran 
• 25779-13-9 (S)-1-phenyl-1,2-ethanediol 
• 158271-95-5 1-(2-hydroxy-1-phenylethyl)-1,5-dihydropyrrol-2-one 
• 56613-80-0 D-2-phenylglycinol 
• 241466-60-4 (R)-(+)-N-(1-phenyl-2-hydroxyethyl)succinimide 

Downstream Products

• 362045-69-0 (5R)-butyl-1-(2-hydroxy-(1'R)-phenylethyl)-pyrrolidin-2-one 
• 1264297-89-3 C₁₄H₁₅NO₄ 
• 1264298-03-4 C₁₉H₁₇N₃O₃ 
• 1264297-90-6 C₂₀H₁₇N₃O₈ 
• 241466-63-7 (1S,4S,5R)-4-Allyl-3-((R)-2-hydroxy-1-phenyl-ethyl)-3-aza-bicyclo[3.1.0]hexan-2-one 
• 241466-62-6 (3R,5aS,6aR,6bS)-3-phenylhexahydro-5H-cyclopropa[3,4]pyrrolo[2,1-b]oxazol-5-one 
• 116830-34-3 (-)-N-<2-(1-Hydroxy-2(R)-phenylethyl)>-5(R)-butyl-2-pyrrolidine 
• 132959-50-3 (5S)-allyl-1-(2-hydroxy-(1'R)-phenylethyl)-pyrrolidin-2-one 
• 241466-61-5 3-phenyl-2,3-dihydro-7aH-pyrrolo[2,1-b]oxazol-5-one 

Relevant articles and documents

Reductive and oxidative transformations of the N-(cyanomethyl)oxazolidine system to expand the chiral pool of piperidines

Two new reactions have been exploited to modify piperidine scaffolds containing the chiral, non-racemic N-(cyanomethyl)oxazolidine system. A Raney nickel mediated decyanation was studied first, followed by an oxidative process using potassium permanganate

Asymmetric synthesis of 5-substituted pyrrolidinones via a chiral N-acyliminium equivalent

5-Substituted pyrrolidinones 5 were synthesized in good yields and with fair to good diastereoselectivities from the chiral non-racemic oxazolopyrrolidinone 4. Various nucleophiles including cuprates, silanes and phosphites were used. The chiral induction

An asymmetric synthesis of the key precursor to (-)-indolizomycin

Using chiral bicyclic lactams, containing an α,β-unsaturation, the key precursor of (-)-indolizomycin was obtained in optically pure form. The sequence involved a >20:1 diastereoselective cyclopropanation of the unsaturated lactam 5 employing sulfoxonium methylide. TiCl4 mediated addition of allyltrimethylsilane afforded pyrrolidone 7 in a diastereomeric ratio of >20:1. The appropriately substituted pyrrolidone 2 was prepared by debenzylation and subsequent alkylation with 3-bromoproponic ester. The six step sequence from commercially available starting materials was performed in 26% overall yield.

Diastereoselective bis-alkylation of chiral non-racemic α,β-unsaturated γ-lactams

A new chiral non-racemic γ-lactam 1 easily prepared in one step from (R)-(-)-phenylglycinol was bis-alkylated α to the carbonyl function in very high to complete diastereoselectivity. The stereochemistry at the so-formed chiral quaternary center was ascertained through an X-ray crystallographic study.