(S)-2-Methyl-CBS-oxazaborolidine supplier

Name
(S)-3,3-Diphenyl-1-methylpyrrolidino[1,2-c]-1,3,2-oxazaborole
EINECS -0
CAS No. 112022-81-8
Article Data18
CAS DataBase
Density 1.12 g/cm³
Solubility Hydrolyzes in water.
Melting Point 115-117 °C
Formula C₁₈H₂₀BNO
Boiling Point 377.544 °C at 760 mmHg
Molecular Weight 277.174
Flash Point 182.133 °C
Transport Information UN 1294 3/PG 2
Appearance white or cream white solid
Safety 26
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms 1H,3H-Pyrrolo[1,2-c][1,3,2]oxazaborole,tetrahydro-1-methyl-3,3-diphenyl-, (S)-;(S)-3,3-Diphenyl-1-methylpyrrolidino[1,2-c]-1,3,2-oxazaborole;(S)-Tetrahydro-1-methyl-3,3-diphenyl-1H,3H-pyrrolo[1,2-c][1,3,2]oxazaborole;(3aS)-Tetrahydro-1-methyl-3,3-diphenyl-1H,3H-pyrrolo[1,2-c][1,3,2]oxazaborole;
PSA 12.47000
LogP 3.48070

Synthetic route

: 151293-60-6
methylbis(diisopropylamino)borane

: 22348-32-9
(R)-α,α-diphenylprolinol

: 112022-81-8
(S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole

Conditions

Conditions	Yield
In tetrahydrofuran; toluene reflux for 30 min; solvents are removed;	89%

: 22348-32-9, 63401-04-7, 112022-88-5, 112068-01-6
(S)-diphenylprolinol

: methylboronic acid

: 112022-81-8
(S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole

Conditions

Conditions	Yield
In toluene byproducts: H2O; refluxing of pyrrolidine deriv. and methylboronic acid in toluene for 3 h; evapn. of solvent in vac.;	86%
With 4 A molecular sieve In toluene byproducts: H2O; react. of pyrrolidine deriv. and methylboronic acid in toluene at 23°C in presence of molecular sieves within 1,5 h; evapn. of solvent in vac.;	86%

: 13061-96-6
dihydroxy-methyl-borane

: 22348-32-9
(R)-α,α-diphenylprolinol

: 112022-81-8
(S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole

Conditions

Conditions	Yield
In n-heptane at 40℃; Solvent; Temperature; Inert atmosphere; Reflux; Large scale;	83%

: 22348-32-9, 63401-04-7, 112022-88-5, 112068-01-6
(S)-diphenylprolinol

: 13061-96-6
dihydroxy-methyl-borane

: 112022-81-8
(S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole

Conditions

Conditions	Yield
In toluene for 3h; Heating;
With 4 A molecular sieve In toluene for 15h; Heating;
In toluene for 14h; Cyclization; Heating;

: 22348-32-9, 63401-04-7, 112022-88-5, 112068-01-6
(S)-diphenylprolinol

: 823-96-1
Trimethylboroxine

: 112022-81-8
(S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole

Conditions

Conditions	Yield
In toluene at 20℃; for 0.6h;
In toluene
In toluene at 20 - 155℃;

: C22H30BNO2

: 86595-28-0
methyldi-n-butoxyborane

A: 112022-81-8
(S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole

B: 71-36-3
butan-1-ol

Conditions

Conditions	Yield
In toluene for 4h; Heating / reflux;

...Expand

: 149915-80-0
6-phenylsulfanyl-3,4-dihydro-2H-naphthalen-1-one

: 112022-81-8
(S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole

: 895534-20-0
(R)-6-phenylsulfanyl-1,2,3,4-tetrahydro-naphthalen-1-ol

Conditions

Conditions	Yield
Stage #1: 6-phenylsulfanyl-3,4-dihydro-2H-naphthalen-1-one; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole With borane N,N-diethylaniline complex In toluene at 30 - 32℃; for 3h; Stage #2: With hydrogenchloride; methanol; water In toluene for 0.666667h;	98%

: 112022-81-8
(S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole

: 302912-29-4
2,2,2-trifluoro-1-(1,1'-biphenyl-2-yl)ethanone

: 945978-45-0
1-([1,1'-biphenyl]-2-yl)-2,2,2-trifluoroethan-1-ol

Conditions

Conditions	Yield
With hydrogenchloride In tetrahydrofuran; toluene	96%
With hydrogenchloride In tetrahydrofuran; toluene	96%

: 13292-87-0
dimethyl sulfide borane

: 112022-81-8
(S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole

: (3aS)-1-methyl-3, 3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole borane complex

Conditions

Conditions	Yield
In toluene vac. transferring of toluene onto (S)-2-methyl-CBS-oxazaborolidine; addn. of BH3*SMe2 by syringe at -78°C; stirring at room temp. for 2 hand then at -10°C for 5 h; vac. transferring of pentane; pptn., filtration, washing with pentane; removal of volatiles in vac., drying overnight;	91%

BH3.S(CH3)2: BH3.S(CH3)2

: (S)-oxazaborolidine

: 60-29-7
diethyl ether

: 25564-22-1
2-pentyl-2-cyclopenten-1-one

: 112022-81-8
(S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole

A: (+)-(1R)-2-pentyl-1-cyclopenten-1-ol

B: 202530-97-0
(R)-2-pentyl-2-cyclopentenol

Conditions

Conditions	Yield
With hydrogenchloride In tetrahydrofuran; methanol; toluene	A n/a B 89%

...Expand

: 160539-64-0
Sn(C4H9)3(CH3)2C3HO

: 112022-81-8
(S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole

: Sn(C4H9)3(CH3)2C3H2(OH)

Conditions

Conditions	Yield
With benzo[1,3,2]dioxaborole In toluene -30°C to -20°C;	85%

: C20H16O7

: 112022-81-8
(S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole

: C20H18O7

Conditions

Conditions	Yield
Stage #1: (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole With dimethylsulfide borane complex In tetrahydrofuran; toluene at 0℃; for 0.25h; Stage #2: C20H16O7 In tetrahydrofuran at -78 - 20℃; for 1h; stereoselective reaction;	85%

: 112022-81-8
(S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole

: 22348-32-9, 63401-04-7, 112022-88-5, 112068-01-6
(S)-diphenylprolinol

Conditions

Conditions	Yield
With water	77%

: 121-89-1
3-Nitroacetophenone

: 112022-81-8
(S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole

: 76116-24-0
(R)-1-(3-nitrophenyl)ethanol

Conditions

Conditions	Yield
Stage #1: (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole With borane Ν,Ν-diethylaniline complex In toluene at 30℃; for 0.333333h; Inert atmosphere; Stage #2: 3-Nitroacetophenone In toluene at 30℃; for 5.5h;	74%

: 2142-63-4
1-(3-Bromophenyl)ethanone

: 112022-81-8
(S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole

: 52780-14-0, 64382-14-5, 134615-22-8, 134615-24-0
(R)-1-(3-bromophenyl)ethanol

Conditions

Conditions	Yield
With dimethyl sulfide borane In tetrahydrofuran; toluene at 30℃; for 7h;	54%

borane-THF: borane-THF

: 17694-68-7
3-(2-bromoacetyl)pyridine hydrobromide

: 112022-81-8
(S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole

: 391906-07-3
(1R)-2-bromo-1-(3-pyridinyl)-1-ethanol

Conditions

Conditions	Yield
In tetrahydrofuran; methanol	34%
In tetrahydrofuran; methanol	27%

...Expand

: 456-04-2
2-Chloro-4'-fluoroacetophenone

: 112022-81-8
(S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole

: 18511-62-1, 53631-23-5, 134356-73-3, 134356-74-4
4-fluorostyrene oxide

Conditions

Conditions	Yield
With sodium hydroxide In tetrahydrofuran

aqueous potassium carbonate: aqueous potassium carbonate

: 24424-99-5
di-tert-butyl dicarbonate

: 112022-81-8
(S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole

: 357405-01-7
[3-Hydroxy-3-(3-pyridinyl)propyl]carbamic acid, 1,1-dimethylethyl ester

Conditions

Conditions	Yield
With hydrogenchloride; borane In tetrahydrofuran; methanol; toluene	928 mg (73%)

...Expand

: 112022-81-8
(S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole

: 38425-26-2
4-chloro-1-(4-methylphenyl)butan-1-one

: 357443-51-7
R-α-(3-Chloropropyl)-4-methyl-benzenemethanol

Conditions

Conditions	Yield
In tetrahydrofuran; methanol

: {1-[4-(6-Methoxy-pyridin-3-yl)-2-oxo-but-3-enyl]-5(R)-methyl-2-oxo-pyrrolidin-3(S)-yl}-carbamic Acid Tert-butyl Ester

: 13292-87-0
dimethyl sulfide borane

: 112022-81-8
(S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole

: {1-[2(R)-Hydroxy-4-(6-methoxy-pyridin-3-yl)-but-3-enyl]-5(R)-methyl-2-oxo-pyrrolidin-3(S)-yl }-carbamic Acid Tert-butyl Ester

Conditions

Conditions	Yield
In tetrahydrofuran; methanol; dichloromethane; toluene

...Expand

: {1-[4-(2-methyl-pyrimidin-5-yl)-2-oxo-but-3-enyl]-5(R)-methyl-2-oxo-pyrrolidin-3(S)-yl}-carbamic Acid Tert-butyl Ester

: 13292-87-0
dimethyl sulfide borane

: 112022-81-8
(S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole

: {1-[2-Hydroxy-4-(2-methyl-pyrimidin-5-yl)-but-3-enyl]-5(R)-methyl-2-oxo-pyrrolidin-3(S)-yl}-carbamic Acid Tert-butyl Ester

Conditions

Conditions	Yield
In tetrahydrofuran; methanol; dichloromethane; toluene

...Expand

borane-THF: borane-THF

: 2631-72-3
2,4-dichlorophenacyl bromide

: 112022-81-8
(S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole

: 187164-20-1
(S)-2-bromo-1-(2,4-dichlorophenyl)ethan-1-ol

Conditions

Conditions	Yield
In tetrahydrofuran; methanol

...Expand

: 112022-81-8
(S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole

: 191591-86-3
5-[3-[4-(4-fluorophenyl)piperazin-1-yl]propyl]-1-methyl-1,4,5,6,7,8-hexahydropyrrolo[3,2-c]azepine-4,8-dione

: (+)-5-[3-[4-(4-fluorophenyl)piperazin-1-yl]propyl]-8-hydroxy-1-methyl-1,4,5,6,7,8-hexahydropyrrolo[3,2-c]azepin-4-one

Conditions

Conditions	Yield
In toluene

: 33944-98-8
(E)-(phenylsulfinyl)but-3-en-2-one

: 112022-81-8
(S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole

: (R,E)-4-phenylthio-3-buten-2-ol

: 655-32-3
2,2,2-trifluoro-1-(4-fluorophenyl)ethanone

: 112022-81-8
(S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole

: 17556-41-1, 50562-19-1, 131832-02-5
2,2,2-trifluoro-1-(4-fluorophenyl)ethanol

Conditions

Conditions	Yield
With benzo[1,3,2]dioxaborole In dichloromethane at -78℃;	n/a

: 13283-31-3
borane

: 112022-81-8
(S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole

: 461412-21-5, 112022-90-9, 545435-36-7, 452935-20-5, 170081-63-7, 415914-26-0
N(CH2)3CHC(C6H5)2OBCH3(BH3)

Conditions

Conditions	Yield
In tetrahydrofuran react. of oxazaborolidine deriv. and BH3 in soln.; not isolated;

: 768400-09-5
isopropyl 7-{(4R)-4-[(1E)-4,4-difluoro-3-oxo-4-phenylbut-1-en-1-yl]-2-oxo-1,3-oxazinan-3-yl}heptanoate

: 768400-08-4
isopropyl 7-[(4R)-4-formyl-2-oxo-1,3-oxazinan-3-yl]heptanoate

: 112022-81-8
(S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole

: isopropyl 7-{(4R)-4-[(1E)-4,4-difluoro-3-hydroxy-4-phenylbut-1-en-yl]-2-oxo-1,3-oxanzinan-3-yl}heptanoate

Conditions

Conditions	Yield
Stage #1: isopropyl 7-{(4R)-4-[(1E)-4,4-difluoro-3-oxo-4-phenylbut-1-en-1-yl]-2-oxo-1,3-oxazinan-3-yl}heptanoate; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole With benzo[1,3,2]dioxaborole In toluene at -78℃; for 1h; Stage #2: isopropyl 7-[(4R)-4-formyl-2-oxo-1,3-oxazinan-3-yl]heptanoate In toluene at -78℃; for 1h; Stage #3: With hydrogenchloride In water; toluene

...Expand

: 112022-81-8
(S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole

: (S)-methyloxazaborolidine

Conditions

Conditions	Yield
With dimethylsulfide borane complex In toluene at 20℃; for 0.5h;

: 552885-75-3
1-(4′-fluoro[1,1′-biphenyl]-2-yl)ethan-1-one

: 112022-81-8
(S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole

A: C14H13FO

B: C14H13FO

Conditions

Conditions	Yield
Stage #1: (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole With borane-THF In tetrahydrofuran at -30℃; for 1h; Inert atmosphere; Stage #2: 1-(4′-fluoro[1,1′-biphenyl]-2-yl)ethan-1-one In tetrahydrofuran at -30℃; for 1h; Overall yield = 86 %; Overall yield = 1.8 g;	A n/a B n/a

...Expand

(S)-2-Methyl-CBS-oxazaborolidine Specification

The (S)-2-Methyl-CBS-oxazaborolidine, with the CAS registry number 112022-81-8, is also known as (S)-Tetrahydro-1-methyl-3,3-diphenyl-1H,3H-pyrrolo[1,2-c][1,3,2]oxazaborole. It belongs to the product categories of API intermediates; Asymmetric Synthesis; B (Classes of Boron Compounds); B-Bromocatecholborane, etc.; Synthetic Organic Chemistry; Asymmetric Synthesis; Chiral Catalysts, Ligands, and Reagents; Reduction; Organic or inorganic borate. This chemical's molecular formula is C₁₈H₂₀BNO and molecular weight is 277.17. What's more, its systematic name is (3aS)-1-Methyl-3,3-diphenyltetrahydro-3H-pyrrolo[1,2-c][1,3,2]oxazaborole. This chemical is stable at common pressure and temperature, and it should be sealed and stored in a cool and dry place. Moreover, it should be protected from oxides and air.

Physical properties of (S)-2-Methyl-CBS-oxazaborolidine are: (1)#H bond acceptors: 2; (2)#H bond donors: 0; (3)#Freely Rotating Bonds: 2; (4)Polar Surface Area: 12.47 Å²; (5)Index of Refraction: 1.599; (6)Molar Refractivity: 84.241 cm³; (7)Molar Volume: 246.584 cm³; (8)Polarizability: 33.396×10^-24cm³; (9)Surface Tension: 43.68 dyne/cm; (10)Density: 1.124 g/cm³; (11)Flash Point: 182.133 °C; (12)Enthalpy of Vaporization: 62.533 kJ/mol; (13)Boiling Point: 377.544 °C at 760 mmHg; (14)Vapour Pressure: 0 mmHg at 25°C.

When you are using this chemical, please be cautious about it as the following:
It is irritating to eyes, respiratory system and skin. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1)SMILES: O2B(N1CCC[C@H]1C2(c3ccccc3)c4ccccc4)C
(2)Std. InChI: InChI=1S/C18H20BNO/c1-19-20-14-8-13-17(20)18(21-19,15-9-4-2-5-10-15)16-11-6-3-7-12-16/h2-7,9-12,17H,8,13-14H2,1H3/t17-/m0/s1
(3)Std. InChIKey: VMKAFJQFKBASMU-KRWDZBQOSA-N

Product Name

(S)-3,3-Diphenyl-1-methylpyrrolidino[1,2-c]-1,3,2-oxazaborole

Synthetic route

(S)-2-Methyl-CBS-oxazaborolidine Specification

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