(2S,5S)-(-)-2-tert-Butyl-3-methyl-5-benzyl-4-imidazolidinone

Base Information

• Chemical Name: (2S,5S)-(-)-2-tert-Butyl-3-methyl-5-benzyl-4-imidazolidinone
• CAS No.: 346440-54-8
• Molecular Formula: C15H22N2O
• Molecular Weight: 246.352
• Hs Code.: 2933990090
• UNII: 8LC842A6QP
• DSSTox Substance ID: DTXSID30437926
• Nikkaji Number: J1.684.365B
• Wikidata: Q27270710
• Mol file: 346440-54-8.mol

Synonyms:346440-54-8;(2S,5S)-(-)-2-tert-Butyl-3-methyl-5-benzyl-4-imidazolidinone;(2S,5S)-5-Benzyl-2-(tert-butyl)-3-methylimidazolidin-4-one;UNII-8LC842A6QP;(2S,5S)-5-benzyl-2-tert-butyl-3-methylimidazolidin-4-one;8LC842A6QP;Macmillan's imidazolidinone second generation catalyst;5-Benzyl-2-tert-butyl-3-methyl-4-imidazolidinone, (2S,5S)-;(-)-(2S,5S)-5-Benzyl-2-tert-butyl-3-methylimidazolidin-4-one;Macmillan's imidazolidinone catalysts second generation catalyst [MI];(2S,4S)-2-(1,1-Dimethylethyl)-3-methyl-5-(phenylmethyl)-4-imidazolidinone;4-Imidazolidinone, 2-(1,1-dimethylethyl)-3-methyl-5-(phenylmethyl)-, (2S,5S)-;(2S,5S)-2-tert-Butyl-3-methyl-5-(phenylmethyl)-4-imidazolidinone;SCHEMBL816353;DTXSID30437926;SKHPYKHVYFTIOI-JSGCOSHPSA-N;(2S,5S)-5-Benzyl-2-tert-butyl-3-methyl-4-imidazolidinone;(2S,5S)-2-tert-Butyl-3-methyl-5-phenylmethyl-4-imidazolidinone;MFCD03426982;AKOS015888860;AS-71003;BP-12919;B4138;CS-0093648;T70804;J-019688;Q27270710;(2S,5S)-5-benzyl-2-tert-butyl-3-methyl-imidazolidm-4-one;1-Methyl-2beta-tert-butyl-4beta-benzyl-5-oxoimidazolidine;(2S,5S)-5-benzyl-2-tert-butyl-3-methyl-imidazolidin-4-one;(2S,5S)-(-)-5-Benzyl-2-tert-butyl-3-methyl-4-imidazolidinone;(2S,5S)-(-)-2-tert-Butyl-3-methyl-5-benzyl-4-imidazolidinone, 97%;(2S,5S)-2-(1?,1?-dimethylethyl)-3-methyl-5-phenylmethyl-4-imidazolidinone

Chemical Property of (2S,5S)-(-)-2-tert-Butyl-3-methyl-5-benzyl-4-imidazolidinone

Chemical Property:

• Melting Point: 93-100 °C(lit.)
• Boiling Point: 378.0±35.0 °C(Predicted)
• PKA: 5.59±0.60(Predicted)
• Flash Point: 182.4oC
• PSA: 32.34000
• Density: 1.040±0.06 g/cm3(Predicted)
• LogP: 2.29820
• Storage Temp.: Inert atmosphere,Room Temperature
• XLogP3: 3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 246.173213330
• Heavy Atom Count: 18
• Complexity: 302

Purity/Quality:

98% ^*data from raw suppliers

(2s,5s)-(-)-2-tert-Butyl-3-methyl-5-benzyl-4-imidazolidinone ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)(C)C1NC(C(=O)N1C)CC2=CC=CC=C2
• Isomeric SMILES: CC(C)(C)[C@H]1N[C@H](C(=O)N1C)CC2=CC=CC=C2
• Uses: (2S,5S)-(-)-2-tert-Butyl-3-methyl-5-benzyl-4-imidazolidinone is a second-generation MacMillan catalyst, which can be used as a chiral organocatalyst in: The chiral transformation reaction, including Friedel-Crafts and Mukaiyama-Michael reactions. The preparation of substituted spiroundecenetriones via asymmetric domino Knoevenagel/Diels-Alder reactions. The asymmetric synthesis of β-hydroxy aldehydes and their dimethylacetals via aldehyde-aldehyde aldol condensation reaction. The enantioselective α-fluorination of aldehydes using N-fluorobenzenesulfonamide as a fluorinating agent. The stereoselective preparation of (oxomethyl)oxabicyclo[3.2.1]octenones and tricyclic pyrroles via [4+3] cycloaddition of (trialkylsiloxy)pentadienals to furans.

Technology Process of (2S,5S)-(-)-2-tert-Butyl-3-methyl-5-benzyl-4-imidazolidinone

There total 14 articles about (2S,5S)-(-)-2-tert-Butyl-3-methyl-5-benzyl-4-imidazolidinone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 58.0%

L-phenylalanine methylamide (35373-92-3) + pivalaldehyde (630-19-3) → (2R,5S)-5-benzyl-2-tert-butyl-3-methylimidazolin-4-one hydrochloride (691847-46-8,390766-89-9) + (2S,5S)-5-benzyl-2-(tert-butyl)-3-methylimidazolidin-4-one (346440-54-8,390766-89-9)

Guidance literature:

With ytterbium(III) triflate; In chloroform; for 8h; Inert atmosphere; Reflux;

DOI:10.1002/chem.201500270

Reference yield: 25.0%

L-phenylalanine methylamide (35373-92-3) + pivalaldehyde (630-19-3) → (2S,5S)-5-benzyl-2-(tert-butyl)-3-methylimidazolidin-4-one (346440-54-8,390766-89-9)

Guidance literature:

With iron(III) chloride; In tetrahydrofuran; for 24h; Molecular sieve; Inert atmosphere; Reflux;

DOI:10.3762/bjoc.8.160

Reference yield: 22.0%

(2R,5S)-5-benzyl-2-tert-butyl-3-methylimidazolin-4-one hydrochloride (691847-46-8,390766-89-9) → (2S,5S)-5-benzyl-2-(tert-butyl)-3-methylimidazolidin-4-one (346440-54-8,390766-89-9)

Guidance literature:

With iron(III) chloride; In tetrahydrofuran; at 20 ℃; for 14h;

DOI:10.1021/ja025981p

upstream raw materials:

L-phenylalanine methylamide

pivalaldehyde

(2R,5S)-5-benzyl-2-tert-butyl-3-methylimidazolin-4-one hydrochloride

methyl (2S)-2-amino-3-phenylpropanoate

Downstream raw materials:

(2S,5S)-5-benzyl-2-(tert-butyl)-3-methyl-4-oxoimidazolidin-1-ium Tetrafluoroborate

(2R,5S)-5-benzyl-2-tert-butyl-3-methylimidazolin-4-one hydrochloride

thiophene

furan

Refernces

• 1、 An, Feng,Maji, Biplab,Min, Elizabeth,Ofial, Armin R.,Mayr, Herbert. "Basicities and Nucleophilicities of Pyrrolidines and Imidazolidinones Used as Organocatalysts". supporting information. p. 1526 - 1547. Retrieved 2020/02/04.
• 2、 Holland, Mareike C.,Metternich, Jan Benedikt,Daniliuc, Constantin,Schweizer, W. Bernd,Gilmour, Ryan. "Aromatic Interactions in Organocatalyst Design: Augmenting Selectivity Reversal in Iminium Ion Activation". supporting information. p. 10031 - 10038. Retrieved 2015/07/07.