(R)-N-Boc-2,2-dimethyl-4-vinyloxazolidine

Base Information

• Chemical Name: (R)-N-Boc-2,2-dimethyl-4-vinyloxazolidine
• CAS No.: 115378-31-9
• Molecular Formula: C12H21NO3
• Molecular Weight: 227.304
• European Community (EC) Number: 806-041-8
• DSSTox Substance ID: DTXSID50446878
• Nikkaji Number: J624.380K
• Wikidata: Q76416104
• Mol file: 115378-31-9.mol

Synonyms:115378-31-9;(R)-N-BOC-2,2-DIMETHYL-4-VINYLOXAZOLIDINE;tert-butyl (4R)-4-ethenyl-2,2-dimethyl-1,3-oxazolidine-3-carboxylate;(R)-2,2-Dimethyl-4-vinyl-oxazolidine-3-carboxylic acid tert-butyl ester;MFCD18074306;SCHEMBL1370603;DTXSID50446878;SEDZCRLQHSPEFD-SECBINFHSA-N;tert-butyl (R)-2,2-dimethyl-4-vinyloxazolidine-3-carboxylate;AKOS024262877;AS-36018;CS-0135787;A907148;(4R)-2,2-Dimethyl-3-(tert-butoxycarbonyl)-4alpha-vinyloxazolidine;3-Oxazolidinecarboxylic acid, 4-ethenyl-2,2-dimethyl-, 1,1-dimethylethyl ester, (4R)-

Chemical Property of (R)-N-Boc-2,2-dimethyl-4-vinyloxazolidine

Chemical Property:

• Boiling Point: 291.8±40.0 °C(Predicted)
• PKA: -2.22±0.60(Predicted)
• PSA: 38.77000
• Density: 1.046±0.06 g/cm3(Predicted)
• LogP: 2.48230
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 227.15214353
• Heavy Atom Count: 16
• Complexity: 291

Purity/Quality:

97% ^*data from raw suppliers

(R)-N-Boc-2,2-dimethyl-4-vinyloxazolidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(N(C(CO1)C=C)C(=O)OC(C)(C)C)C
• Isomeric SMILES: CC1(N([C@@H](CO1)C=C)C(=O)OC(C)(C)C)C

Technology Process of (R)-N-Boc-2,2-dimethyl-4-vinyloxazolidine

There total 2 articles about (R)-N-Boc-2,2-dimethyl-4-vinyloxazolidine 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:

tert-butyl 4-formyl-2,2-dimethyloxazolidine-3-carboxylate (95715-87-0,102308-32-7,144070-30-4,127589-93-9) + diazomethyl-trimethyl-silane (18107-18-1) → tert-butyl (4R)-2,2-dimethyl-4-vinyloxazolidine-3-carboxylate (115378-31-9) + tert-butyl (4S)-2,2-dimethyl-4-vinyl-1,3-oxazolidine-3-carboxylate (133625-87-3)

Guidance literature:

With Rh(PPh₃)3Cl; triphenylphosphine; In tetrahydrofuran; isopropyl alcohol; at 25 ℃; for 4h; Title compound not separated from byproducts;

DOI:10.1002/1521-3773(20010803)40:15<2887::AID-ANIE2887>3.0.CO;2-Q

Reference yield:

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine (95715-87-0) + Methylenetriphenylphosphorane (19493-09-5) → tert-butyl (4R)-2,2-dimethyl-4-vinyloxazolidine-3-carboxylate (115378-31-9) + tert-butyl (4S)-2,2-dimethyl-4-vinyl-1,3-oxazolidine-3-carboxylate (133625-87-3)

Guidance literature:

In tetrahydrofuran; hexane; at 25 ℃; for 4h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1021/jo00013a023

Reference yield: 94.0%

1-bromo-4-methoxy-benzene (104-92-7) + tert-butyl (4R)-2,2-dimethyl-4-vinyloxazolidine-3-carboxylate (115378-31-9) → tert-butyl (4R)-4-[2-(4-methoxyphenyl)ethyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate (240420-43-3)

Guidance literature:

tert-butyl (4R)-2,2-dimethyl-4-vinyloxazolidine-3-carboxylate; With 9-borabicyclo[3.3.1]nonane dimer; In toluene; at 80 - 85 ℃; for 0.5h;

1-bromo-4-methoxy-benzene; With sodium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetra-(n-butyl)ammonium iodide; In toluene; at 90 ℃; Further stages.;

DOI:10.1021/ol005645i

upstream raw materials:

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine

Methylenetriphenylphosphorane

tert-butyl 4-formyl-2,2-dimethyloxazolidine-3-carboxylate

diazomethyl-trimethyl-silane

Downstream raw materials:

tert-butyl [(1S)-1-(hydroxymethyl)prop-2-en-1-yl]carbamate

(R)-2-(N-tert-butoxycarbonylamino)-3-buten-1-ol

tert-butyl (4R)-4-(2-hydroxyethyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate

tert-butyl (4S)-4-[1-hydroxyethyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate

Refernces

• 1、 Beaulieu, Pierre L.,Duceppe, Jean-Simon,Johnson, Carolyne. "Synthesis of Chiral Vinylglycines". . p. 4196 - 4204. Retrieved 2007/10/02.