(S)-2-Methyl-CBS-oxazaborolidine

Base Information

• Chemical Name: (S)-2-Methyl-CBS-oxazaborolidine
• CAS No.: 112022-81-8
• Molecular Formula: C18H20BNO
• Molecular Weight: 277.174
• Hs Code.: 29349990
• DSSTox Substance ID: DTXSID60370458
• Nikkaji Number: J370.864K
• Wikidata: Q72489106
• Mol file: 112022-81-8.mol

Synonyms:112022-81-8;(S)-2-Methyl-CBS-oxazaborolidine;(S)-Methyl Oxazaborolidine;(S)-3,3-Diphenyl-1-methylpyrrolidino[1,2-c]-1,3,2-oxazaborole;(S)-(-)-2-Methyl-CBS-oxazaborolidine;(S)-1-Methyl-3,3-diphenylhexahydropyrrolo[1,2-c][1,3,2]oxazaborole;(S)-5,5-Diphenyl-2-methyl-3,4-propano-1,3,2-oxazaborolidine;(3aS)-1-methyl-3,3-diphenyl-3a,4,5,6-tetrahydropyrrolo[1,2-c][1,3,2]oxazaborole;(S)-Me-CBS;S-(-)-2-Methyl-CBS-oxazaborolidine;(S)-Tetrahydro-1-methyl-3,3-diphenyl-1H,3H-pyrrolo[1,2-c][1,3,2]oxazaborole;(S)-1-Methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2c][1,3,2]oxazaborole;(S)-3,3-Diphenyl-1-methyltetrahydro-3H-pyrrolo[1,2-c][1,3,2]oxazaborole;(S)-2-Methyl-CBS-oxazaborolidine (1 M in Toluene);MFCD00078439;C18H20BNO;(S)-Methyl-CBS-oxazaborolidine;(S)-tetrahydro-1-methyl-3,3-diphenyl-1H,3H-pyrrolo(1,2-c)(1,3,2)oxazaborole;(S)-3,3-Diphenyl-1-methyltetrahydro-1H,3H-pyrrolo[1,2-c][1,3,2]oxazaborole;(S)-Me-CBS Catalyst;(S)-METHYL-CBS;SCHEMBL263582;SCHEMBL3311840;(S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole;1-Methyl-3,3-diphenyltetrahydro-3H-pyrrolo[1,2-c][1,3,2]oxazaborole #;DTXSID60370458;(S)-2-methyl-CBS oxazaborolidine;BCP11653;AKOS015840981;AC-9535;AM62743;DS-3373;SC10773;(S)-(?)-2-Methyl-CBS-oxazaborolidine;(S)-2-methyl-CBS-oxazaborolidine(THF);(S)-(-)-2-methyl-CBS- oxazaborolidine;D2131;D5912;F11434;EN300-7396289;(S)-(-)-2-Methyl-CBS-oxazaborolidine, >=95%;(S)-2-METHYL-CBS-OXAZABOROLIDINE MONOHYDRATE;Q-101082;a,a-Diphenyl-L-prolinol methylboronic acid cycl-amide ester;(S)-5,5-Diphenyl-2-methyl-3,4-propano-1,3,2oxazaborolidine;(3aS)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole;(S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2] oxazaborole;(S)-1-methyl-3,3-diphenylhexahydropyrrolo-[1,2-c][1,3,2]oxazaborole;(3aS)-1-Methyl-3,3-diphenyltetrahydro-1H,3H-pyrrolo[1,2-c][1,3,2]oxazaborole;(3AS)-1-METHYL-3,3-DIPHENYLTETRAHYDRO-3H-PYRROLO[1,2-C][1,3,2]OXAZABOROLE;(3as)-tetrahydro-1-methyl-3,3-diphenyl-3h-pyrrolo[1,2-c][1,3,2]oxazaborole;(S)-1-methyl-3,3-diphenyl-3a,4,5,6-tetrahydropyrrolo[1,2-c][1,3,2]oxazaborole;(S)-3,3-diphenyl-1-methyltetrahydro-1H,3H-pyrrolo[1,2-c] [1,3,2] oxazaborol;(S)-3,3-diphenyl-1-methyltetrahydro-1H,3H-pyrrolo[1,2-c][1,3,2] oxazaborol;(S)-3,3-Diphenyl-1-methyltetrahydro-1H,3H-pyrrolo[1,2-c][1,3,2]oxazaborole 1M in toluene;(S)-3,3-diphenyl-1-methyltetrahydro-1H,3H-pyrrolo[1,2-c]1,3,2 oxazaborol;(S)-5,5-Diphenyl-2-methyl-3,4-propano-1,3,2-oxazaborolidine (ca. 1mol/L in Toluene);(S)-tetrahydro-1-methyl-3,3-diphenyl-1 H,3 H-pyrrolo[1,2-c][1,3,2] oxazaborole;(S)-tetrahydro-1-methyl-3,3-diphenyl-1 H,3H-pyrrolo[1,2-c]-[1,3,2]oxazaborole;(S)-tetrahydro-1-methyl-3,3-diphenyl-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-, (3aS)-;(S)-Tetrahydro-1-methyl-3,3-diphenyl-1H,3H-pyrrolo[1,2-c][1,3,2]oxazaborole, 0.9-1.1M in toluene;(S)-Tetrahydro-1-methyl-3,3-diphenyl-1H,3H-pyrrolo[1,2-c][1,3,2]oxazaborole, 0.9-1.1M in toluene [(S)-Methyloxazaborolidine] Corey Catalyst

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

Chemical Property:

• Appearance/Colour: white or cream white solid
• Vapor Pressure: 6.7E-06mmHg at 25°C
• Melting Point: 115-117 °C
• Refractive Index: -68 ° (C=1, MeOH)
• Boiling Point: 377.544 °C at 760 mmHg
• PKA: 1.02±0.40(Predicted)
• Flash Point: 182.133 °C
• PSA: 12.47000
• Density: 1.12 g/cm³
• LogP: 3.48070
• Storage Temp.: Refrigerator
• Sensitive.: Air & Moisture Sensitive
• Water Solubility.: Hydrolyzes 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

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

Safty Information:

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

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: (S)-2-Methyl-CBS-oxazaborolidine is used as an oxazaborolidine catalyst. It is also employed 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 an anhydrous catalyst for 'CBS' reduction reaction. suzuki reaction

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

There total 7 articles about (S)-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%

methylbis(diisopropylamino)borane (151293-60-6) + (R)-α,α-diphenylprolinol (22348-32-9) → (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole (112022-81-8,133261-83-3)

Guidance literature:

In tetrahydrofuran; toluene; reflux for 30 min; solvents are removed;

DOI:10.1016/0022-328X(93)80377-N

Reference yield: 86.0%

(S)-diphenylprolinol (22348-32-9,63401-04-7,112022-88-5,112068-01-6) + methylboronic acid → (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole (112022-81-8,133261-83-3)

Guidance literature:

In toluene; byproducts: H2O; refluxing of pyrrolidine deriv. and methylboronic acid in toluene for 3 h; evapn. of solvent in vac.;

DOI:10.1021/ja00259a075

Reference yield: 83.0%

dihydroxy-methyl-borane (13061-96-6) + (R)-α,α-diphenylprolinol (22348-32-9) → (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole (112022-81-8,133261-83-3)

Guidance literature:

In n-heptane; at 40 ℃; Solvent; Temperature; Inert atmosphere; Reflux; Large scale;

upstream raw materials:

(S)-diphenylprolinol

dihydroxy-methyl-borane

Trimethylboroxine

methyldi-n-butoxyborane

Downstream raw materials:

(R)-6-phenylsulfanyl-1,2,3,4-tetrahydro-naphthalen-1-ol

(1R)-2-bromo-1-(3-pyridinyl)-1-ethanol

(R)-2-pentyl-2-cyclopentenol

N(CH₂)3CHC(C₆H₅)2OBCH₃(BH₃)

Refernces

• 1、 Cobb, Kelsey M.,Rabb-Lynch, Javon M.,Hoerrner, Megan E.,Manders, Alex,Zhou, Qi,Watson, Mary P.. "Stereospecific, Nickel-Catalyzed Suzuki-Miyaura Cross-Coupling of Allylic Pivalates to Deliver Quaternary Stereocenters". supporting information. p. 4355 - 4358. Retrieved 2017/08/23.
• 2、 Kutama, Ibrahim U.,Jones, Simon. "Enantioselective Desymmetrization of Glutarimides Catalyzed by Oxazaborolidines Derived from cis-1-Amino-indan-2-ol". . p. 11468 - 11479. Retrieved 2015/12/04.