(R)-2-METHYL-CBS-OXAZABOROLIDINE

Base Information

• Chemical Name: (R)-2-METHYL-CBS-OXAZABOROLIDINE
• CAS No.: 133261-83-3
• Molecular Formula: C18H20BNO
• Molecular Weight: 277.17
• Mol file: 133261-83-3.mol

Synonyms:ALPHA,ALPHA-DIPHENYL-D-PROLINOL METHYLBORONIC ACID CYCL-AMIDE-ESTER;(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]OXAZOBOROLE;(R)-METHYL OXAZABOROLIDINE;(R)-ME CBS;(R)-2-METHYL-CBS-OXAZABOROLIDINE MONOHYDRATE;(R)-3,3-DIPHENYL-1-METHYLTETRAHYDRO-1H,3H-PYRROLO[1,2-C][1,3,2]OXAZABOROLE;(R)-3,3-DIPHENYL-1-METHYLTETRAHYDRO-3H-PYRROLO-[1,2-C][1,3,2]OXAZABOROLE

Chemical Property of (R)-2-METHYL-CBS-OXAZABOROLIDINE

Chemical Property:

• Melting Point: 85-95 °C(lit.)
• Boiling Point: 377.544 °C at 760 mmHg
• PKA: 1.02±0.40(Predicted)
• Flash Point: 182.133 °C
• PSA: 12.47000
• Density: 1.124 g/cm³
• LogP: 3.48070
• Storage Temp.: 2-8°C

Purity/Quality:

98%,99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s): F,Xn
• Hazard Codes: F,Xn
• Statements: 11-38-48/20-63-65-67
• Safety Statements: 36/37-62

MSDS Files:

Useful:

Technology Process of (R)-2-METHYL-CBS-OXAZABOROLIDINE

There total 12 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%

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: 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: 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

upstream raw materials:

(S)-diphenylprolinol

dihydroxy-methyl-borane

Trimethylboroxine

methyldi-n-butoxyborane

Downstream raw materials:

(S)-α-(2-Chloroethyl)-5-isoxazolemethanol

C₁₀H₂₁NO₃

(R)-1-(3-bromophenyl)ethanol

(R)-1-(3-nitrophenyl)ethanol

Refernces

• 1、 -. "Chiral MeCBS synthesis process". Paragraph 0015; 0016. . Retrieved 2017/04/20.
• 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.