112022-83-0

Basic information

• Product Name: (R)-3,3-Diphenyl-1-methylpyrrolidino[1,2-c]-1,3,2-oxazaborole
• Synonyms: ALPHA,ALPHA-DIPHENYL-D-PROLINOL METHYLBORONIC ACID CYCL-AMIDE-ESTER;(R)-(+)-2-METHYL-CBS-OXAZABOROLIDINE;(R)-2-METHYL-CBS-OXAZABOROLIDINE;(R)-2-METHYL-CBS-OXAZABOROLIDINE MONOHYDRATE;(R)-1-METHYL,3,3-DIPHENYL-TETRAHYDRO-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)-3,3-DIPHENYL-1-METHYLTETRAHYDRO-3H-PYRROLO-[1,2-C][1,3,2]OXAZABOROLE;(R)-5,5-DIPHENYL-2-METHYL-3,4-PROPANO-1,3,2-OXAZABOROLIDINE
• CAS NO: 112022-83-0
• Molecular Formula: C₁₈H₂₀BNO
• Molecular Weight: 277.17
• EINECS: -0
• Product Categories: 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
• Mol File: 112022-83-0.mol

Chemical Properties

• Melting Point: 85-95 °C(lit.)
• Boiling Point: 111 °C
• Flash Point: 40 °F
• Appearance: Colorless to amber/Liquid
• Density: 0.95 g/mL at 25 °C
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 68 ° (C=1, MeOH)
• Storage Temp.: 2-8°C
• PKA: 1.02±0.40(Predicted)
• Water Solubility: Not miscible or difficult to mix in water.
• Sensitive: Air & Moisture Sensitive
• BRN: 9059874
• CAS DataBase Reference: (R)-3,3-Diphenyl-1-methylpyrrolidino[1,2-c]-1,3,2-oxazaborole(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-3,3-Diphenyl-1-methylpyrrolidino[1,2-c]-1,3,2-oxazaborole(112022-83-0)
• EPA Substance Registry System: (R)-3,3-Diphenyl-1-methylpyrrolidino[1,2-c]-1,3,2-oxazaborole(112022-83-0)

Safety Data

• 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
• RIDADR: UN 1294 3/PG 2
• WGK Germany: 3
• F: 10
• HazardClass: 3
• PackingGroup: II
• Hazardous Substances Data: 112022-83-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(R)-3,3-Diphenyl-1-methylpyrrolidino[1,2-c]-1,3,2-oxazaborole is used as a catalyst in the asymmetric reduction of prochiral ketones for the enantioselective synthesis of α-hydroxy acids, α-amino acids, C2 symmetrical ferrocenyl diols, and propargyl alcohols. These synthesized compounds are essential in the development of pharmaceuticals with improved efficacy and reduced side effects.
Used in Chemical Synthesis:
In the field of chemical synthesis, (R)-3,3-Diphenyl-1-methylpyrrolidino[1,2-c]-1,3,2-oxazaborole is used as a CBS catalyst for asymmetric reduction and asymmetric synthesis. This allows for the production of stereospecific motifs such as α-hydroxy acids, α-amino acids, symmetrical ferrocenyl diols, and propargyl alcohols, which are crucial in the creation of complex molecules with specific properties.
Used in Suzuki Reaction:
(R)-3,3-Diphenyl-1-methylpyrrolidino[1,2-c]-1,3,2-oxazaborole is also used in the Suzuki reaction, a cross-coupling reaction between an organoboron compound and an organic halide or pseudo-halide. This reaction is widely employed in the synthesis of complex organic molecules, including pharmaceuticals, agrochemicals, and advanced materials.
Overall, (R)-3,3-Diphenyl-1-methylpyrrolidino[1,2-c]-1,3,2-oxazaborole plays a significant role in various industries, particularly in the pharmaceutical and chemical synthesis sectors, due to its ability to catalyze important reactions and facilitate the production of essential compounds.

Reactions

Convenient catalyst for the enantioselective borane reduction of ketones at ambient temperatures. Asymmetric synthesis of α-chiral hydroxyalkylphosphines via a catalytic, enantioselective reduction of acylphosphines. Nickel-catalyzed cross-couplings of benzylic pivalates with arylboroxines: Stereospecific formation of diarylalkanes and triarylmethanes. Enantioselective reduction of prochiral ketones with NaBH4/Me2SO4/(S)-Me-CBS.

InChI:InChI=1/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-/m1/s1

Synthetic route

(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)

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

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)

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

dihydroxy-methyl-borane (13061-96-6) + (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)

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

bis(methoxy)methylborane (7318-81-2) + (R)-α,α-diphenylprolinol (22348-32-9) → methanol (67-56-1) + (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole (112022-83-0)

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

methyl 3-(4-methoxybenzoyl)propionate (5447-74-5) + (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole (112022-83-0) → (S)-methyl 4-hydroxy-4-(4’-methoxyphenyl)butyrate (848044-56-4)

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

C51H60O7Si + (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole (112022-83-0) → C51H62O7Si

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 + dimethyl sulfide borane (13292-87-0) + (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole (112022-83-0) → methyl 2,4-dihydroxy-6-(3-((2R,6R)-6-methyltetrahydro-2H-pyran-2-yl)-2-oxopropyl) benzoate

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%

8-benzyloxy-5-(2-bromoacetyl)-1H-quinolin-2-one (100331-89-3) + (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole (112022-83-0) → 8-(benzyloxy)-5-[(1R)-2-bromo-1-hydroxyethyl]quinolin-2(1H)-one (530084-79-8)

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

3-chloro-1-(3-isoxazolyl)-1-propanone (357405-87-9) + (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole (112022-83-0) → (S)-α-(2-Chloroethyl)-5-isoxazolemethanol (357405-40-4)

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

dimethyl sulfate (77-78-1) + (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole (112022-83-0) → (R)-(+)-1-methyl-α,α-diphenyl-2-pyrrolidinemethanol (144119-12-0)

Conditions	Yield
With potassium carbonate In water

(3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole (112022-83-0) → borane complex of (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole

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

[14C]-Sch 57871 (191330-56-0) + (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole (112022-83-0) → (3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone (163222-32-0)

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;

{4-[(R)-2-Oxo-5-((E)-3-oxo-oct-1-enyl)-pyrrolidin-1-yl]-butoxy}-acetic acid methyl ester (492471-65-5) + (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole (112022-83-0) → {4-[(R)-2-((E)-(S)-3-hydroxy-oct-1-enyl)-5-oxo-pyrrolidin-1-yl]-butoxy}-acetic acid methyl ester (492471-64-4)

Conditions	Yield
With hydrogenchloride In methanol; toluene

methyl 4-[(2-{(5R)-2-oxo-5-[(1E)-3-oxooct-1-enyl] pyrrolidin-1-yl} ethyl)thio]-butanoate (492471-48-4) + (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole (112022-83-0) → 4-[(2-{(2R)-2-[(1E,3S)-3-Hydroxyoct-1-enyl]-5-oxopyrrolidin-1-yl}-ethyl)thio] Butanoic Acid Methyl Ester

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 + (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole (112022-83-0) → ethyl 7-[(2R)-2-{(1E,3S)-3-hydroxy-4-(3-chlorophenyl)-1-buten-1-yl}-5-oxo-1-pyrrolidinyl]heptanoate (533893-55-9)

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 + (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole (112022-83-0) → 7-{2R-[3S-hydroxy-4-(3-trifluoromethyl-phenyl)-but-1-enyl]-5-oxo-pyrrolidin-1-yl}-heptanoic acid ethyl ester

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 + (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole (112022-83-0) → 7-{2R-[3S-hydroxy-4-(3-chloro-phenyl)-but-1-enyl]-5-oxo-pyrrolidin-1-yl}-heptanenitrile

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 + (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole (112022-83-0) → 7-{2R-[3S-hydroxy-4-(3-methoxymethyl-phenyl)-but-1-enyl]-5-oxo-pyrrolidin-1-yl}-heptanoic acid ethyl ester

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 + (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole (112022-83-0) → 7-{2R-[3S-hydroxy-4-(3-trifluoromethoxy-phenyl)-but-1-enyl]-5-oxo-pyrrolidin-1-yl}-heptanoic acid ethyl ester

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 + (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole (112022-83-0) → 7-{2R-[4-(3-bromo-phenyl)-3S-hydroxy-but-1-enyl]-5-oxo-pyrrolidin-1-yl}-heptanoic acid ethyl ester

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 + (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole (112022-83-0) → 7-(2R-{3S-hydroxy-4-[3-(2-methoxy-ethyl)-phenyl]-but-1-enyl}-5-oxo-pyrrolidin-1-yl)-heptanoic acid ethyl ester

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 + (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole (112022-83-0) → 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	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 + (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole (112022-83-0) → 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	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 + (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole (112022-83-0) → 7-{2R-[3S-hydroxy-4-(3-methoxymethyl-phenyl)-but-1-enyl]-5-oxo-pyrrolidin-1-yl}-heptanenitrile

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

3-(2-bromoacetyl)pyridine hydrobromide (17694-68-7) + (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole (112022-83-0) → 3-[(2R)-oxiranyl]pyridine (174060-40-3)

methanol (67-56-1) + (3R,4S)-4-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]azetidin-2-one (190595-65-4) + (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole (112022-83-0) → (3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone (163222-32-0)

Conditions	Yield
With hydrogenchloride In tetrahydrofuran

sodium hydrogencarbonate (144-55-8) + 1-(4-Fluorophenyl)piperazine (2252-63-3) + 5-(3-chloropropyl)-1-methyl-1,4,5,6,7,8-hexahydro-pyrrolo[3,2-c]azepine-4,8-dione (191591-69-2) + (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole (112022-83-0) → (-)-(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	Yield
With potassium iodide; sodium chloride; potassium carbonate In ethyl acetate; toluene; acetonitrile

methyl 7-(4-fluorophenyl)-7-oxoheptanoate + (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole (112022-83-0) → methyl (S)-7-(4-fluorophenyl)-7-hydroxyheptanoate (156558-16-6)

Conditions	Yield
In tetrahydrofuran; methanol

Cyclopentyl (4-t-butyldimethylsilyloxy-1,3-dihydro-6-ethyl-7-methyl-3-oxoisobenzofuran-5-yl methyl)methanone (171490-00-9) + (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole (112022-83-0) → (S)-2-(4-t-butyldimethylsilyloxy-1,3-dihydro-6-ethyl-7-methyl-3-oxoisobenzofuran-5-yl)-1-cyclopentenyl-1-hydroxyethane (171490-01-0)

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 + (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole (112022-83-0) → (S)-4-[3-(5-Methyl-2-phenyl-4-oxazolyl)-1-hydroxypropyl]bromobenzene (147641-94-9)

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

Upstream product

• 13061-96-6 dihydroxy-methyl-borane 
• 22348-32-9 (R)-α,α-diphenylprolinol 
• 7318-81-2 bis(methoxy)methylborane 
• 22348-32-9 (S)-diphenylprolinol 
• 823-96-1 Trimethylboroxine 

Downstream Products

• 144119-12-0 (R)-(+)-1-methyl-α,α-diphenyl-2-pyrrolidinemethanol 
• 163222-32-0 (3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone 
• 357405-40-4 (S)-α-(2-Chloroethyl)-5-isoxazolemethanol 
• 533893-55-9 ethyl 7-[(2R)-2-{(1E,3S)-3-hydroxy-4-(3-chlorophenyl)-1-buten-1-yl}-5-oxo-1-pyrrolidinyl]heptanoate 
• 174060-40-3 3-[(2R)-oxiranyl]pyridine 
• 191592-36-6 (-)-(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 
• 156558-16-6 methyl (S)-7-(4-fluorophenyl)-7-hydroxyheptanoate 
• 147641-94-9 (S)-4-[3-(5-Methyl-2-phenyl-4-oxazolyl)-1-hydroxypropyl]bromobenzene 
• 173365-07-6 (S)-3-chloro-1-(4-methylphenyl)propan-1-ol 
• 530084-79-8 8-(benzyloxy)-5-[(1R)-2-bromo-1-hydroxyethyl]quinolin-2(1H)-one 
• 662111-36-6 4-(benzyloxy)-7-[(1R)-2-bromo-1-hydroxyethyl]-1,3-benzothiazol-2(3H)-one 
• 848044-56-4 (S)-methyl 4-hydroxy-4-(4’-methoxyphenyl)butyrate 

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The invention provides novel β2 adrenergic receptor agonist compounds of formula (I): wherein R1-R13 and w have any of the values described in the specification. The invention also provides combinations of such compounds and other therapeutic agents, pharmaceutical compositions comprising such compounds and combinations, methods of using such compounds to treat diseases associated with β2 adrenergic receptor activity, and processes and intermediates useful for preparing such compounds.

Synthesis of 3H, 14C and 13C6 labelled Sch 58235

3H-Sch 58235 was prepared at a specific activity of 29.1 Ci/mmol by Ir(COD)(Cy3P)PyPF6 catalysed exchange with tritium gas. 14C-Sch 58235 was prepared in three steps from p-hydroxy[ring-U-14C]benzaldehyde with an overall radiochemical yield of 21%. 13C6-Sch 58235 was similarly prepared in three steps from p-hydroxy[ring-U-13C6]benzaldehyde in an overall yield of 41%. Copyright