92841-65-1

Usage

Uses

Employed in the synthesis of optically active mono-, di-, and trihydroxy compounds.

InChI:InChI=1/C11H14N2O/c1-8-10(12-11(14)13(8)2)9-6-4-3-5-7-9/h3-8,10H,1-2H3,(H,12,14)/t8-,10-/m0/s1

Upstream product

• 4785-79-9 1,3-dihydro-1,5-dimethyl-4-phenyl-2H-imidazol-2-one 
• 90-81-3 ephedrine 
• 57-13-6 urea 
• 128863-72-9 (4R,5S)-1,5-Dimethyl-3-((R)-3-methyl-hex-5-enoyl)-4-phenyl-imidazolidin-2-one 
• 25394-33-6 (-)-Chloroephedrine 
• 67-56-1 methanol 
• 176018-06-7 (4S,5R)-1-((R)-2-Benzylamino-propionyl)-3,4-dimethyl-5-phenyl-imidazolidin-2-one 
• 98-88-4 benzoyl chloride 
• 260784-00-7 (4R,5S,2'R,2''S)-1,5-dimethyl-3-[3'-(2''-acetamido-4''-methylpentanoyl)amino-2'-hydroxypropionyl]-4-phenylimidazolidin-2-one 
• 50-98-6 ephedrine hydrochloride 
• 206358-46-5 (2'RS,4S,5R)-1-N-(2'-iodopropanoyl)-3,4-dimethyl-5-phenylimidazolidin-2-one 
• 197232-68-1 (4R,5S,3'R)-1,5-dimethyl-3-(2'-acetamido-3'-hydroxypropionyl)-4-phenylimidazolidin-2-one 
• 206358-56-7 (4S,5R)-1-((R)-2-Benzylamino-hexanoyl)-3,4-dimethyl-5-phenyl-imidazolidin-2-one 
• 206358-53-4 (4S,5R)-1-((R)-2-Benzylamino-butyryl)-3,4-dimethyl-5-phenyl-imidazolidin-2-one 

Downstream Products

• 691873-17-3 (4R,5S)-1-methyl-3-<1-((p-methylphenyl)sulfonyl)methyl>-4-phenyl-5-methylimidazolidin-2-one 
• 132659-19-9 (4S,5R)-1-cyano-3,4-dimethyl-5-phenylimidazolidin-2-one 
• 128947-01-3 (4R,5S)-3-[(2E)-2-butenoyl]-1,5-dimethyl-4-phenyl-2-imidazolidinone 
• 139962-51-9 (4R,5S)-1,5-Dimethyl-3-((E)-pent-2-enoyl)-4-phenyl-imidazolidin-2-one 
• 331283-86-4 (4R,5S)-4-cyclohexyl-1,5-dimethyl-3-(2-propenoyl)-2-imidazolidinone 
• 142061-15-2 (4R,5S)-1,5-dimethyl-4-cyclohexyl-2-imidazolidinone 
• 143359-26-6 (4S,5R)-1-Acetyl-3,4-dimethyl-5-phenyl-imidazolidin-2-one 
• 128947-02-4 (4R,5S)-1,5-dimethyl-3-[(2E)-3-phenyl-2-propenoyl]-4-phenyl-2-imidazolidinone 
• 176791-94-9 (4S,5R)-1-((E)-2-Bromo-but-2-enoyl)-3,4-dimethyl-5-phenyl-imidazolidin-2-one 
• 182355-97-1 (4S,5R)-1-((E)-3-Biphenyl-4-yl-acryloyl)-3,4-dimethyl-5-phenyl-imidazolidin-2-one 
• 252580-15-7 (4R,5S)-1,5-Dimethyl-3-[(3'-N-benzoylamino)propanoyl]-4-phenylimidazolidin-2-one 
• 317845-50-4 (4R,5S,1'S)-1,5-dimethyl-3-[1-(phenylsulfonyl)-6-chlorohexyl]-4-phenylimidazolidin-2-one 
• 317845-52-6 (4R,5R,1'S)-1,5-dimethyl-3-[1-(phenylsulfonyl)-5-benzyloxypentyl]-4-phenylimidazolidin-2-one 
• 370064-63-4 (E)-1,5-(S)-dimethyl-3-(5-methylhex-2-enoyl)-4-(R)-phenylimidazolidin-2-one 

Relevant academic research and scientific papers

Intramolecular carbolithiation of heterosubstituted alkynes: An experimental and theoretical study

A series of heterosubstitued alkynes was successfully submitted to the intramolecular carbolithiation of their triple bond. We show that the addition is stereoselective because of the control exerted by the terminal substituent X on the geometry of the transition state. A complementary DFT study suggests that the addition is anti when a strong Li-X interaction occurs.

Stereoselective synthesis of quaternary center bearing azetines and their β-amino acid derivatives

(Chemical Equation Presented) We describe here the use of a stable, four-membered azetine heterocycle for the preparation of highly substituted β-amino acid derivatives. Imidazolidinone chiral auxiliaries were found to eliminate a competitive reaction pathway that had been present under previously reported conditions for azetine synthesis. The ephedrine derived imidazolidin-2-one 21 was allowed to react as its chlorotitanium enolate with O-methyl or -benzyl oximes under optimized conditions to gain improved access to azetines at the gram scale. The azetines were further found to undergo alkylation with complete diastereocontrol, affording the creation of a quaternary center. Subsequent ring opening with benzoyl chloride and auxiliary cleavage provided the corresponding β2,2,3-amino carbonyl derivatives in good yields.

Studies on a urea-directed Stork-Crabtree hydrogenation. Synthesis of the C1-C9 subunit of (+)-zincophorin

(Chemical Equation Presented) A detailed account on the stereoselective synthesis of the C1-C9 subunit of (+)-zincophorin is described here. This approach features the first application of a stereoselective inverse electron demand hetero-[4 + 2] cycloaddi

1,3-Heterazolidines-2-heterounsaturated compounds derived from ephedrines

Herein, a direct and easy method for preparing 2-oxo-, 2-thione- or 2-imine-1,3-heterazolidines derived from ephedrines and norephedrines are reported. The method is based on solvent free heating of ephedrines with oxocyanate or thiocyanate salts (180-200 °C). In the reactions with potassium oxocyanate in refluxing ethanol, it was possible to isolate ureidic derivatives. The structure and stereochemistry of the compounds were determined by 1H, 13C NMR, IR spectroscopies and mass spectrometry. Ureidic derivatives, cis-1,5-dimethyl-4-phenyl-imidazolidine-2-thione and trans-4-methyl-5-phenyl-thiazolidine-2-one are new compounds. Ephedrineurea, cis-1,5-dimethyl-4-phenyl-imidazolidine-2-thione and trans-4-methyl-5-phenyl-thiazolidine-2-one were also studied by X-ray diffraction.

Microwave-assisted ring expansion of N-acetyl 3′-unsubstituted aziridine in the presence of Lewis acids

The microwave-assisted ring expansion of N-acetyl 3′-unsubstituted aziridine-2-imides and N-acetyl 3′-unsubstituted aziridine-2-esters to oxazolines is reported. The regioselectivities of the rearrangements depend upon the reaction conditions, such as the Lewis acid selected and the solvent.

Dipeptides containing D-serine or D-isoserine from the same (R)-aziridine-2-imide by a simple reversal of the synthetic procedure

The ring expansion of 3-unsubstituted (R)-aziridine-2-imide- containing dipeptide under acidic conditions gives rise to oxazoline-5-imide regio and stereoselectively, which can be hydrolysed to the dipeptide containing D-isoserine. On the other hand, the ring opening of 3-unsubstituted (R)-aziridine-2-ester dipeptide, easily obtained from the same (R)-aziridine, gives the regioisomeric dipeptide containing D-serine.

Rationalising diastereoselection in the dynamic kinetic resolution of α-haloacyl imidazolidinones

A crossover from S(N)2 to general base catalysed nucleophilic substitution can account for the dichotomous diastereoselectivity observed in DKR reactions of α-haloacyl imidazolidinones. Aprotic nucleophiles (Nu-) react preferentially with the 5S,2'R diastereomer via an S(N)2 mechanism. Conversely, amines (R2NH) generally react preferentially with the 5S,2'S diastereomer. General base catalysis via a bifurcated hydrogen bonded assembly accounts for this anomalous stereoselectivity.

Synthesis of enantiomerically pure aziridine-2-imides by cyclization of chiral 3-benzyloxyamino imide enolates

Aziridine-2-imides are prepared both in high yield and high diastereoselectivity from chiral 3'-benzyloxyamino imides 2, 3, and 8 by treatment with triethylamine in the presence of either TiCl4 or AlMe2Cl. 2 and 3 are easily obtained

Synthesis of enantiomerically pure trans aziridine-2-carboxylates by diastereoselective Gabriel-Cromwell reaction

Benzyl aziridine-2-carboxylates have been obtained in high yield and selectivity by conjugate addition of ammonia to α,β-unsaturated chiral imides followed by treatment with lithium benzyloxide. A ring-expansion of the aziridine to an oxazoline allowed th