(R)-2-METHYL-CBS-OXAZABOROLIDINE supplier

Name
(R)-3,3-Diphenyl-1-methylpyrrolidino[1,2-c]-1,3,2-oxazaborole
EINECS -0
CAS No. 112022-83-0
Article Data8
CAS DataBase
Density 1.12 g/cm³
Solubility Not miscible or difficult to mix in water.
Melting Point 85-95 ºC
Formula C₁₈H₂₀BNO
Boiling Point 377.5 ºC at 760 mmHg
Molecular Weight 277.174
Flash Point 182.1ºC
Transport Information UN 1294 3/PG 2
Appearance white to light yellow crystal powder
Safety 36/37-62-33-29-16-2
Risk Codes 11-38-48/20-63-65-67-36/37-19
Molecular Structure
Hazard Symbols F,Xn,Xi
Synonyms (3aR)-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-, (R)-;(R)-Me-CBS;(R)-Me-Corey-Bakshi-Shibatareagent;(R)-Methyl-CBS;(R)-Tetrahydro-1-methyl-3,3-diphenyl-1H,3H-pyrrolo[1,2-c][1,3,2]oxazaborole;(R-Methyl-Corey-Bakshi-Shibata catalyst;
PSA 12.47000
LogP 3.48070

Synthetic route

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

: 13061-96-6
dihydroxy-methyl-borane

: 112022-83-0
(3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole

Conditions

Conditions	Yield
In hexane at 30℃; Solvent; Temperature; Inert atmosphere; Reflux;	81%

: 823-96-1
Trimethylboroxine

: 22348-32-9
(R)-α,α-diphenylprolinol

: 112022-83-0
(3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole

Conditions

Conditions	Yield
In toluene Heating;
With borane In toluene at 20 - 150℃; for 4.5h;
In toluene at 20℃; for 0.5h;

: 13061-96-6
dihydroxy-methyl-borane

: 22348-32-9
(R)-α,α-diphenylprolinol

: 112022-83-0
(3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole

Conditions

Conditions	Yield
With 4 A molecular sieve In toluene at 20℃; for 1h;	80 mg
In toluene Reflux; Dean-Stark;

: 7318-81-2
bis(methoxy)methylborane

: 22348-32-9
(R)-α,α-diphenylprolinol

A: 67-56-1
methanol

B: 112022-83-0
(3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole

Conditions

Conditions	Yield
In toluene at 20℃; for 1h; Product distribution / selectivity;

...Expand

: 5447-74-5
methyl 3-(4-methoxybenzoyl)propionate

: 112022-83-0
(3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole

: 848044-56-4
(S)-methyl 4-hydroxy-4-(4’-methoxyphenyl)butyrate

Conditions

Conditions	Yield
With boron trifluoride-tetrahydrofuran complex In toluene at -78℃;	96%

: C51H60O7Si

: 112022-83-0
(3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole

: C51H62O7Si

Conditions

Conditions	Yield
With borane-THF In tetrahydrofuran; toluene at -40℃; for 2h;	95%

: methyl 2,4-bis(methoxymethoxy)-6-(3-((2R,6R)-6-methyltetrahydro-2H-pyran-2-yl)-2-oxopropyl) benzoate

: 13292-87-0
dimethyl sulfide borane

: 112022-83-0
(3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole

: methyl 2,4-dihydroxy-6-(3-((2R,6R)-6-methyltetrahydro-2H-pyran-2-yl)-2-oxopropyl) benzoate

Conditions

Conditions	Yield
Stage #1: dimethyl sulfide borane; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole In tetrahydrofuran at 0℃; for 0.5h; Stage #2: methyl 2,4-bis(methoxymethoxy)-6-(3-((2R,6R)-6-methyltetrahydro-2H-pyran-2-yl)-2-oxopropyl) benzoate In tetrahydrofuran at -20℃; for 12h; Reagent/catalyst;	90%

...Expand

: 100331-89-3
8-benzyloxy-5-(2-bromoacetyl)-1H-quinolin-2-one

: 112022-83-0
(3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole

: 530084-79-8
8-(benzyloxy)-5-[(1R)-2-bromo-1-hydroxyethyl]quinolin-2(1H)-one

Conditions

Conditions	Yield
In tetrahydrofuran; hydrogenchloride; ethyl acetate liquid HCl;	76%

: 357405-87-9
3-chloro-1-(3-isoxazolyl)-1-propanone

: 112022-83-0
(3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole

: 357405-40-4
(S)-α-(2-Chloroethyl)-5-isoxazolemethanol

Conditions

Conditions	Yield
With borane In tetrahydrofuran; methanol; toluene	13%

: 77-78-1
dimethyl sulfate

: 112022-83-0
(3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole

: 144119-12-0
(R)-(+)-1-methyl-α,α-diphenyl-2-pyrrolidinemethanol

Conditions

Conditions	Yield
With potassium carbonate In water

: 112022-83-0
(3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole

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

Conditions

Conditions	Yield
With dimethylsulfide borane complex In toluene at 20℃; for 2h;

: 191330-56-0
[14C]-Sch 57871

: 112022-83-0
(3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole

: 163222-32-0
(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone

Conditions

Conditions	Yield
Stage #1: [14C]-Sch 57871; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole In tetrahydrofuran at -20℃; for 0.0833333h; Stage #2: With dimethylsulfide borane complex In tetrahydrofuran at -20℃; for 1.5h;

: 492471-65-5
{4-[(R)-2-Oxo-5-((E)-3-oxo-oct-1-enyl)-pyrrolidin-1-yl]-butoxy}-acetic acid methyl ester

: 112022-83-0
(3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole

: 492471-64-4
{4-[(R)-2-((E)-(S)-3-hydroxy-oct-1-enyl)-5-oxo-pyrrolidin-1-yl]-butoxy}-acetic acid methyl ester

Conditions

Conditions	Yield
With hydrogenchloride In methanol; toluene

: 492471-48-4
methyl 4-[(2-{(5R)-2-oxo-5-[(1E)-3-oxooct-1-enyl] pyrrolidin-1-yl} ethyl)thio]-butanoate

: 112022-83-0
(3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole

: 4-[(2-{(2R)-2-[(1E,3S)-3-Hydroxyoct-1-enyl]-5-oxopyrrolidin-1-yl}-ethyl)thio] Butanoic Acid Methyl Ester

Conditions

Conditions	Yield
With hydrogenchloride In methanol; toluene

: 7-[2S-[4-(3-Chloro-phenyl)-3-oxo-but-1-enyl]-5-oxo-pyrrolidin-1-yl]-heptanoic acid, ethyl ester

: 112022-83-0
(3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole

: 533893-55-9
ethyl 7-[(2R)-2-{(1E,3S)-3-hydroxy-4-(3-chlorophenyl)-1-buten-1-yl}-5-oxo-1-pyrrolidinyl]heptanoate

Conditions

Conditions	Yield
With hydrogenchloride; sodium hydroxide; benzo[1,3,2]dioxaborole In tetrahydrofuran; dichloromethane; ethyl acetate; toluene

: 7-{2-oxo-5R-[3-oxo-4-(3-trifluoromethyl-phenyl)-but-1-enyl]-pyrrolidin-1-yl}-heptanoic acid ethyl ester

: 112022-83-0
(3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole

: 7-{2R-[3S-hydroxy-4-(3-trifluoromethyl-phenyl)-but-1-enyl]-5-oxo-pyrrolidin-1-yl}-heptanoic acid ethyl ester

Conditions

Conditions	Yield
With hydrogenchloride; sodium hydroxide; benzo[1,3,2]dioxaborole In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; toluene

: 7-{2R-[4-(3-chloro-phenyl)-3-oxo-but-1-enyl]-5-oxo-pyrrolidin-1-yl}-heptanenitrile

: 112022-83-0
(3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole

: 7-{2R-[3S-hydroxy-4-(3-chloro-phenyl)-but-1-enyl]-5-oxo-pyrrolidin-1-yl}-heptanenitrile

Conditions

Conditions	Yield
With hydrogenchloride; benzo[1,3,2]dioxaborole In tetrahydrofuran; methanol; dichloromethane; toluene

: 7-{2R-[4-(3-methoxymethyl-phenyl)-3-oxo-but-1-enyl]-5-oxo-pyrrolidin-1-yl}-heptanoic acid ethyl ester

: 112022-83-0
(3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole

: 7-{2R-[3S-hydroxy-4-(3-methoxymethyl-phenyl)-but-1-enyl]-5-oxo-pyrrolidin-1-yl}-heptanoic acid ethyl ester

Conditions

Conditions	Yield
With hydrogenchloride; benzo[1,3,2]dioxaborole In tetrahydrofuran; methanol; dichloromethane; toluene

: 7-{2-oxo-5R-[3-oxo-4-(3-trifluoromethoxy-phenyl)-but-1-enyl]-pyrrolidin-1-yl}-heptanoic acid ethyl ester

: 112022-83-0
(3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole

: 7-{2R-[3S-hydroxy-4-(3-trifluoromethoxy-phenyl)-but-1-enyl]-5-oxo-pyrrolidin-1-yl}-heptanoic acid ethyl ester

Conditions

Conditions	Yield
With benzo[1,3,2]dioxaborole In tetrahydrofuran; methanol; dichloromethane; chloroform; ethyl acetate; toluene

: 7-{2R-[4-(3-bromo-phenyl)-3-oxo-but-1-enyl]-5-oxo-pyrrolidin-1-yl}-heptanoic acid ethyl ester

: 112022-83-0
(3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole

: 7-{2R-[4-(3-bromo-phenyl)-3S-hydroxy-but-1-enyl]-5-oxo-pyrrolidin-1-yl}-heptanoic acid ethyl ester

Conditions

Conditions	Yield
With hydrogenchloride; benzo[1,3,2]dioxaborole In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; toluene

: 7-(2R-{4-[3-(2-Methoxy-ethyl)-phenyl]-3-oxo-but-1-enyl}-5-oxo-pyrrolidin-1yl)-heptanoic acid ethyl ester

: 112022-83-0
(3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole

: 7-(2R-{3S-hydroxy-4-[3-(2-methoxy-ethyl)-phenyl]-but-1-enyl}-5-oxo-pyrrolidin-1-yl)-heptanoic acid ethyl ester

Conditions

Conditions	Yield
With hydrogenchloride; benzo[1,3,2]dioxaborole In tetrahydrofuran; dichloromethane; ethyl acetate; toluene

: 5-(3-{2R-[4-(4-fluoro-phenyl)-3-oxo-but-1-enyl]-5-oxo-pyrrolidin-1-yl}-propyl)-thiophene-2-carboxylic acid methyl ester

: 112022-83-0
(3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole

: 5-(3-{2R-[4-(4-fluoro-phenyl)-3S-hydroxy-but-1-enyl]-5-oxo-pyrrolidin-1-yl}-propyl)-thiophene-2-carboxylic acid methyl ester

Conditions

Conditions	Yield
With benzo[1,3,2]dioxaborole In tetrahydrofuran; methanol; chloroform; toluene

: 5-(3-{2R-[4-(3-chloro-phenyl)-3-oxo-but-1-enyl]-5-oxo-pyrrolidin-1-yl}-propyl)-thiophene-2-carboxylic acid methyl ester

: 112022-83-0
(3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole

: 5-(3-{2R-[4-(3-chloro-phenyl)-3S-hydroxy-but-1-enyl]-5-oxo-pyrrolidin-1-yl}-propyl)-thiophene-2-carboxylic acid methyl ester

Conditions

Conditions	Yield
With benzo[1,3,2]dioxaborole In tetrahydrofuran; methanol; sodium hydroxide; CH2Cl2was; dichloromethane; ethyl acetate; toluene

: 7-{2R-[4-(3-methoxymethyl-phenyl)-3-oxo-but-1-enyl]-5-oxo-pyrrolidin-1-yl}-heptanenitrile

: 112022-83-0
(3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole

: 7-{2R-[3S-hydroxy-4-(3-methoxymethyl-phenyl)-but-1-enyl]-5-oxo-pyrrolidin-1-yl}-heptanenitrile

Conditions

Conditions	Yield
With hydrogenchloride; benzo[1,3,2]dioxaborole In tetrahydrofuran; methanol; dichloromethane; toluene

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

: 112022-83-0
(3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole

: 174060-40-3
3-[(2R)-oxiranyl]pyridine

: 67-56-1
methanol

: 190595-65-4
(3R,4S)-4-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]azetidin-2-one

: 112022-83-0
(3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole

: 163222-32-0
(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone

Conditions

Conditions	Yield
With hydrogenchloride In tetrahydrofuran

...Expand

: 144-55-8
sodium hydrogencarbonate

: 2252-63-3
1-(4-Fluorophenyl)piperazine

: 191591-69-2
5-(3-chloropropyl)-1-methyl-1,4,5,6,7,8-hexahydro-pyrrolo[3,2-c]azepine-4,8-dione

: 112022-83-0
(3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole

: (-)-(S)-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
With potassium iodide; sodium chloride; potassium carbonate In ethyl acetate; toluene; acetonitrile

...Expand

: methyl 7-(4-fluorophenyl)-7-oxoheptanoate

: 112022-83-0
(3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole

: 156558-16-6
methyl (S)-7-(4-fluorophenyl)-7-hydroxyheptanoate

Conditions

Conditions	Yield
In tetrahydrofuran; methanol

: 171490-00-9
Cyclopentyl (4-t-butyldimethylsilyloxy-1,3-dihydro-6-ethyl-7-methyl-3-oxoisobenzofuran-5-yl methyl)methanone

: 112022-83-0
(3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole

: 171490-01-0
(S)-2-(4-t-butyldimethylsilyloxy-1,3-dihydro-6-ethyl-7-methyl-3-oxoisobenzofuran-5-yl)-1-cyclopentenyl-1-hydroxyethane

Conditions

Conditions	Yield
With hydrogenchloride; dimethylsulfide; borane In dichloromethane; toluene
With hydrogenchloride; dimethylsulfide; borane In dichloromethane; toluene

: 4-[3-(5-Methyl-2-phenyl-4-oxazolyl)propionyl]bromobenzene

: 112022-83-0
(3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole

: 147641-94-9
(S)-4-[3-(5-Methyl-2-phenyl-4-oxazolyl)-1-hydroxypropyl]bromobenzene

Conditions

Conditions	Yield
silica gel In tetrahydrofuran; methanol; hexane; dichloromethane; water	87%, >99%

(R)-2-METHYL-CBS-OXAZABOROLIDINE Chemical Properties

MF: C₁₈H₂₀BNO
MW: 277.17
Appearance: white to light yellow crystal powde
mp: 85-95 °C(lit.)
bp: 111 °C
density: 0.95 g/mL at 25 °C
refractive index: 68 ° (C=1, MeOH)
Fp: 40 °F
storage temp.: 2-8°C
Sensitive: Air & Moisture Sensitive

(R)-2-METHYL-CBS-OXAZABOROLIDINE Safety Profile

Hazard Codes: F,Xn,Xi
Risk Statements: 11-38-48/20-63-65-67-36/37-19
Safety Statements: 36/37-62-33-29-16-2
RIDADR: UN 1294 3/PG 2
F: 10
HazardClass: 3
PackingGroup: II

Product Name

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

Synthetic route

(R)-2-METHYL-CBS-OXAZABOROLIDINE Chemical Properties

(R)-2-METHYL-CBS-OXAZABOROLIDINE Safety Profile

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