(R)-2-Methyl-CBS-oxazaborolidine

Base Information

• Chemical Name: (R)-2-Methyl-CBS-oxazaborolidine
• CAS No.: 112022-83-0
• Molecular Formula: C18H20BNO
• Molecular Weight: 277.174
• Hs Code.: 29319090
• European Community (EC) Number: 601-151-0,443-530-1
• UNII: 4WZ68942D5
• DSSTox Substance ID: DTXSID40920652
• Nikkaji Number: J382.975H
• Wikipedia: (R)-2-Methyl-CBS-oxazaborolidine
• Wikidata: Q4544847
• Mol file: 112022-83-0.mol

Synonyms:112022-83-0;(R)-2-Methyl-CBS-oxazaborolidine;(R)-METHYL OXAZABOROLIDINE;(R)-(+)-2-Methyl-CBS-oxazaborolidine;(R)-1-methyl-3,3-diphenylhexahydropyrrolo[1,2-c][1,3,2]oxazaborole;(R)-5,5-Diphenyl-2-methyl-3,4-propano-1,3,2-oxazaborolidine;(R)-Tetrahydro-1-methyl-3,3-diphenyl-1H,3H-pyrrolo[1,2-c][1,3,2]oxazaborole;(3aR)-1-methyl-3,3-diphenyl-3a,4,5,6-tetrahydropyrrolo[1,2-c][1,3,2]oxazaborole;(R)-3,3-Diphenyl-1-methyltetrahydro-3H-pyrrolo[1,2-c][1,3,2]oxazaborole;(R)-(+)-2-Methyl-CBS-oxazaborolidine (1 M in Toluene);(R)-5,5-DIPHENYL-2-METHYL-3,4-PROPANO-1,3,2-OXAZABORLIDINE;MFCD00078440;(3aR)-1-methyl-3,3-diphenyltetrahydro-3H-pyrrolo[1,2-c][1,3,2]oxazaborole;(R)-3,3-Diphenyl-1-methyltetrahydro-1H,3H-pyrrolo[1,2-c][1,3,2]oxazaborole;1H,3H-Pyrrolo[1,2-c][1,3,2]oxazaborole, tetrahydro-1-methyl-3,3-diphenyl-, (3aR)-;(3aR)-1-Methyl-3,3-diphenyl-3a,4,5,6-tetrahydropyrrolo[1,2-c][1,3,2]oxazaborole (1mol/L in Toluene);C18H20BNO;(R)-3,3-Diphenyl-1-methylpyrrolidino[1,2-c]-1,3,2-oxazaborole;Corey's catalyst;R-MeCBS;(R) -CBS catalyst;(R)-Me-CBS Catalyst;(R)-METHYL-CBS;(R)-ME CBS;2-Methyl-CBS-oxazaborolidine;SCHEMBL177308;SCHEMBL522527;(R)-methyl CBS oxazaborolidine;DTXSID40920652;VMKAFJQFKBASMU-QGZVFWFLSA-N;(R)-2-Methyl-CBS-oxazaboro-lidine;(R)-Me-corey-bakshi-shibata reagent;2-Methyl-cbs-oxazaborolidine, (R)-;BBL103109;STL556919;(R)-1-Methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole;(R)-METHYL-CBS-OXAZABOROLIDINE;AKOS015841145;AKOS015968991;4WZ68942D5;AC-9534;AM62744;SC10770;(R)-1-methyl-3,3-diphenyltetrahydro-1H,3H-pyrrolo[1,2-c][1,3,2]oxazaborole;(R)-2-methyl-CBS-oxazaborolidine(THF);(R)-(+)-2-methyl-CBS- oxazaborolidine;(R)-Methyl oxazaborolidine 1M in toluene;AS-47015;D2130;D5911;Methyl coreybakshishibata catalyst: (R)-form;F11419;(R)-(+)-2-Methyl-CBS-oxazaborolidine, >=95%;(R)-Methyloxazaborolidine, 0.9-1.1M in toluene;A852890;Methyl coreybakshishibata catalyst: (R)-form [MI];(R)-2-METHYL-CBS-OXAZABOROLIDINE MONOHYDRATE;Q-101081;Q4544847;a,a-Diphenyl-D-prolinol methylboronic acid cycl-amide ester;(R)-5,5-Diphenyl-2-methyl-3,4-propano-1,3,2oxazaborolidine;(R)-1-Methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2c][1,3,2]oxazaborole;(R)-1-methyl-3,3-diphenyltetrahydro-3H-pyrrolo[1,2-c][1,3,2]oxazaborole;(3aR)-Tetrahydro-1-methyl-3,3-diphenyl-1H,3H-pyrrolo(1,2-C)(1,3,2)oxazaborole;(3aR)-tetrahydro-1-methyl-3,3-diphenyl-3H-pyrrolo[1,2-c][1,3,2]oxazaborole;(R)-1-methyl-3,3-diphenyltetrahydro-3H-pyrrolo[1,2-c] [1,3,2] oxazaborole;(R)-3,3-diphenyl-1-methyltetrahydro-1H,3H-pyrrolo[1,2-c] [1,3,2]oxazaborole;(R)-5,5-Diphenyl-2-methyl-3,4-propano-1,3,2-oxazaborolidine (ca. 1mol/L in Toluene);(r)-tetrahydro-1-methyl-3,3-diphenyl-(1h,3h)-pyrrolo[1,2-c][1,3,2]-oxazaborole;(r)-tetrahydro-1-methyl-3,3-diphenyl-1h, 3h-pyrrolo[1,2-c][1,3,2]oxazaborole;(R)-tetrahydro-1-methyl-3,3-diphenyl-1H,3H-pyrrolo [1,2-c][1,3,2]oxazaborole;(r)-tetrahydro-1-methyl-3,3-diphenyl-1h,3h-pyrrolo-[1,2-c][1,3,2]oxazaborole;(R)-tetrahydro-1-methyl-3,3-diphenyl-1H,3H-pyrrolo[1,2-c] [1,3,2]-oxazaborole;(R)-tetrahydro-1-methyl-3,3-diphenyl-1H,3H-pyrrolo[1,2-c]-[1,3,2]oxazaborole;(R)-TETRAHYDRO-1-METHYL-3,3-DIPHENYL-1H,3H-PYRROLO[1,2-C][1,3,2] OXAZABOROLE;(R)-tetrahyro-1-methyl-3,3-diphenyl-1H,3H-pyrrolo[1,2-c] [1,3,2]-oxazaborole;(3aR)-1-Methyl-3,3-diphenyltetrahydro-3H-pyrrolo(1,2-C)(1,3,2)oxazaborole(R)-2-methyl-cbs-oxazaborolidine(R)-me-cbs;(R)-1-methyl-3,3-diphenyltetrahydro-1H,3H-pyrrolo[1,2-c][1,3,2]oxazaborole, 1M in Toluene;(R)-Tetrahydro-1-methyl-3,3-diphenyl-1H,3H-pyrrolo[1,2-c][1,3,2]oxazaborole, 0.9-1.1M in toluene [(R)-Methyloxazaborolidine] Corey Catalyst

Chemical Property of (R)-2-Methyl-CBS-oxazaborolidine

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 85-95 ºC
• Refractive Index: 68 ° (C=1, MeOH)
• Boiling Point: 377.5 ºC at 760 mmHg
• PKA: 1.02±0.40(Predicted)
• Flash Point: 182.1ºC
• PSA: 12.47000
• Density: 1.12 g/cm³
• LogP: 3.48070
• Storage Temp.: 2-8°C
• Sensitive.: Air & Moisture Sensitive
• Water Solubility.: Not miscible or difficult to mix in water.
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 277.1637944
• Heavy Atom Count: 21
• Complexity: 344

Purity/Quality:

99% ^*data from raw suppliers

(R)-(+)-2-Methyl-CBS-oxazaborolidine(1MinToluene) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F,Xn,Xi
• Hazard Codes: F,Xn,Xi
• Statements: 11-38-48/20-63-65-67-36/37-19-40
• Safety Statements: 36/37-62-33-29-16-2-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(N2CCCC2C(O1)(C3=CC=CC=C3)C4=CC=CC=C4)C
• Isomeric SMILES: B1(N2CCC[C@@H]2C(O1)(C3=CC=CC=C3)C4=CC=CC=C4)C
• Uses: suzuki reaction (R)-2-Methyl-CBS-oxazaborolidine is used in the asymmetric reduction of prochiral ketones. Other applications include the enantioselective synthesis of α-hydroxy acids, α-amino acids, C2 symmetrical ferrocenyl diols, and propargyl alcohols. It is also used in a desymmetrizing reduction leading to (S)-4-hydroxycyclohexenone. It is useful in the production of stereospecific motifs such as α-hydroxy acids, α-amino acids, symmetrical ferrocenyl diols and propargyl alcohols. CBS Catalysts for Asymmetric Reduction and Asymmetric Synthesis

Technology Process of (R)-2-Methyl-CBS-oxazaborolidine

There total 5 articles about (R)-2-Methyl-CBS-oxazaborolidine 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: 89.0%

→ (1S)-2-bromo-1-[3-(3,4-dichlorophenyl)isoxazol-5-ylmethanol + (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole (112022-83-0,133261-83-3)

Guidance literature:

Reference yield: 81.0%

(S)-diphenylprolinol (22348-32-9,63401-04-7,112022-88-5,112068-01-6) + dihydroxy-methyl-borane (13061-96-6) → (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole (112022-83-0,133261-83-3)

Guidance literature:

In hexane; at 30 ℃; Solvent; Temperature; Inert atmosphere; Reflux;

Reference yield:

Trimethylboroxine (823-96-1) + (R)-α,α-diphenylprolinol (22348-32-9) → (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole (112022-83-0,133261-83-3)

Guidance literature:

In toluene; Heating;

DOI:10.1002/jlcr.539

upstream raw materials:

Trimethylboroxine

(R)-α,α-diphenylprolinol

dihydroxy-methyl-borane

bis(methoxy)methylborane

Downstream raw materials:

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone

methyl (S)-7-(4-fluorophenyl)-7-hydroxyheptanoate

8-(benzyloxy)-5-[(1R)-2-bromo-1-hydroxyethyl]quinolin-2(1H)-one

(S)-methyl 4-hydroxy-4-(4’-methoxyphenyl)butyrate

Refernces

• 1、 -. "Chiral MeCBS synthesis process". Paragraph 0013; 0014. . Retrieved 2017/04/20.
• 2、 Furkert, Daniel P.,Husbands, Stephen M.. "First asymmetrie synthesis of frans-3,4-dimethyl-4-arylpiperidines". . p. 3769 - 3771. Retrieved 2008/02/14.