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112022-83-0 Usage

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.

Chemical Properties

white to light yellow crystal powde

Uses

Different sources of media describe the Uses of 112022-83-0 differently. You can refer to the following data:
1. suzuki reaction
2. (R)-2-Methyl-CBS-oxazaborolidine is used 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 also used in a desymmetrizing reduction leading to (S)-4-hydroxycyclohexenone. It is useful in the production of stereospecific motifs such as α-hydroxy acids, α-amino acids, symmetrical ferrocenyl diols and propargyl alcohols.
3. CBS Catalysts for Asymmetric Reduction and Asymmetric Synthesis

Check Digit Verification of cas no

The CAS Registry Mumber 112022-83-0 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,1,2,0,2 and 2 respectively; the second part has 2 digits, 8 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 112022-83:
(8*1)+(7*1)+(6*2)+(5*0)+(4*2)+(3*2)+(2*8)+(1*3)=60
60 % 10 = 0
So 112022-83-0 is a valid CAS Registry Number.
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

112022-83-0 Well-known Company Product Price

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  • TCI America

  • (D2130)  (R)-5,5-Diphenyl-2-methyl-3,4-propano-1,3,2-oxazaborolidine  >97.0%(T)

  • 112022-83-0

  • 1g

  • 990.00CNY

  • Detail
  • TCI America

  • (D2130)  (R)-5,5-Diphenyl-2-methyl-3,4-propano-1,3,2-oxazaborolidine  >97.0%(T)

  • 112022-83-0

  • 5g

  • 3,860.00CNY

  • Detail
  • Alfa Aesar

  • (L14582)  (R)-2-Methyl-CBS-oxazaborolidine, 1M soln. in toluene   

  • 112022-83-0

  • 1ml

  • 386.0CNY

  • Detail
  • Alfa Aesar

  • (L14582)  (R)-2-Methyl-CBS-oxazaborolidine, 1M soln. in toluene   

  • 112022-83-0

  • 5ml

  • 838.0CNY

  • Detail
  • Alfa Aesar

  • (L14582)  (R)-2-Methyl-CBS-oxazaborolidine, 1M soln. in toluene   

  • 112022-83-0

  • 25ml

  • 2686.0CNY

  • Detail
  • Alfa Aesar

  • (L09230)  (R)-2-Methyl-CBS-oxazaborolidine monohydrate, 94%   

  • 112022-83-0

  • 250mg

  • 835.0CNY

  • Detail
  • Alfa Aesar

  • (L09230)  (R)-2-Methyl-CBS-oxazaborolidine monohydrate, 94%   

  • 112022-83-0

  • 1g

  • 2693.0CNY

  • Detail
  • Aldrich

  • (649317)  (R)-(+)-2-Methyl-CBS-oxazaborolidine  ≥95%

  • 112022-83-0

  • 649317-1G

  • 592.02CNY

  • Detail
  • Aldrich

  • (649317)  (R)-(+)-2-Methyl-CBS-oxazaborolidine  ≥95%

  • 112022-83-0

  • 649317-10G

  • 2,979.99CNY

  • Detail
  • Aldrich

  • (457698)  (R)-(+)-2-Methyl-CBS-oxazaborolidinesolution  1 M in toluene

  • 112022-83-0

  • 457698-5ML

  • 807.30CNY

  • Detail
  • Aldrich

  • (457698)  (R)-(+)-2-Methyl-CBS-oxazaborolidinesolution  1 M in toluene

  • 112022-83-0

  • 457698-25ML

  • 2,671.11CNY

  • Detail
  • Aldrich

  • (674656)  (R)-(+)-2-Methyl-CBS-oxazaborolidinesolution  1 M in THF

  • 112022-83-0

  • 674656-5ML

  • 1,070.90CNY

  • Detail

112022-83-0SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name (R)-2-Methyl-CBS-oxazaborolidine, 1M solution in toluene

1.2 Other means of identification

Product number -
Other names (R)-5,5-Diphenyl-2-methyl-3,4-propano-1,3,2-oxazaborolidine

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:112022-83-0 SDS

112022-83-0Synthetic route

dihydroxy-methyl-borane
13061-96-6

dihydroxy-methyl-borane

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

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

Conditions
ConditionsYield
In hexane at 30℃; Solvent; Temperature; Inert atmosphere; Reflux;81%
Trimethylboroxine
823-96-1

Trimethylboroxine

(R)-α,α-diphenylprolinol
22348-32-9

(R)-α,α-diphenylprolinol

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

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

Conditions
ConditionsYield
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

dihydroxy-methyl-borane

(R)-α,α-diphenylprolinol
22348-32-9

(R)-α,α-diphenylprolinol

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

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

Conditions
ConditionsYield
With 4 A molecular sieve In toluene at 20℃; for 1h;80 mg
In toluene Reflux; Dean-Stark;
bis(methoxy)methylborane
7318-81-2

bis(methoxy)methylborane

(R)-α,α-diphenylprolinol
22348-32-9

(R)-α,α-diphenylprolinol

A

methanol
67-56-1

methanol

B

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

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

Conditions
ConditionsYield
In toluene at 20℃; for 1h; Product distribution / selectivity;
methyl 3-(4-methoxybenzoyl)propionate
5447-74-5

methyl 3-(4-methoxybenzoyl)propionate

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

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

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

(S)-methyl 4-hydroxy-4-(4’-methoxyphenyl)butyrate

Conditions
ConditionsYield
With boron trifluoride-tetrahydrofuran complex In toluene at -78℃;96%
C51H60O7Si

C51H60O7Si

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

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

C51H62O7Si

C51H62O7Si

Conditions
ConditionsYield
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

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

dimethyl sulfide borane
13292-87-0

dimethyl sulfide borane

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

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

Conditions
ConditionsYield
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

8-benzyloxy-5-(2-bromoacetyl)-1H-quinolin-2-one

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

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

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

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

Conditions
ConditionsYield
In tetrahydrofuran; hydrogenchloride; ethyl acetate liquid HCl;76%
3-chloro-1-(3-isoxazolyl)-1-propanone
357405-87-9

3-chloro-1-(3-isoxazolyl)-1-propanone

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

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

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

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

Conditions
ConditionsYield
With borane In tetrahydrofuran; methanol; toluene13%
dimethyl sulfate
77-78-1

dimethyl sulfate

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

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

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

(R)-(+)-1-methyl-α,α-diphenyl-2-pyrrolidinemethanol

Conditions
ConditionsYield
With potassium carbonate In water
(3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole
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

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

Conditions
ConditionsYield
With dimethylsulfide borane complex In toluene at 20℃; for 2h;
[14C]-Sch 57871
191330-56-0

[14C]-Sch 57871

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

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

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

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

Conditions
ConditionsYield
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

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

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

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

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

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

Conditions
ConditionsYield
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

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

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

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

Conditions
ConditionsYield
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

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

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

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

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

Conditions
ConditionsYield
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

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

(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

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

Conditions
ConditionsYield
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

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

(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

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

Conditions
ConditionsYield
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

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

(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

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

Conditions
ConditionsYield
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

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

(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

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

Conditions
ConditionsYield
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

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

(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

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

Conditions
ConditionsYield
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

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

(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

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

Conditions
ConditionsYield
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

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

(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

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
ConditionsYield
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

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

(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

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
ConditionsYield
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

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

(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

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

Conditions
ConditionsYield
With hydrogenchloride; benzo[1,3,2]dioxaborole In tetrahydrofuran; methanol; dichloromethane; toluene
3-(2-bromoacetyl)pyridine hydrobromide
17694-68-7

3-(2-bromoacetyl)pyridine hydrobromide

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

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

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

3-[(2R)-oxiranyl]pyridine

methanol
67-56-1

methanol

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

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

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

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

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

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

Conditions
ConditionsYield
With hydrogenchloride In tetrahydrofuran
sodium hydrogencarbonate
144-55-8

sodium hydrogencarbonate

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

1-(4-Fluorophenyl)piperazine

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

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

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

(-)-(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
ConditionsYield
With potassium iodide; sodium chloride; potassium carbonate In ethyl acetate; toluene; acetonitrile
methyl 7-(4-fluorophenyl)-7-oxoheptanoate

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

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

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

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

methyl (S)-7-(4-fluorophenyl)-7-hydroxyheptanoate

Conditions
ConditionsYield
In tetrahydrofuran; methanol
Cyclopentyl (4-t-butyldimethylsilyloxy-1,3-dihydro-6-ethyl-7-methyl-3-oxoisobenzofuran-5-yl methyl)methanone
171490-00-9

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

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

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

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

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

Conditions
ConditionsYield
With hydrogenchloride; dimethylsulfide; borane In dichloromethane; toluene
With hydrogenchloride; dimethylsulfide; borane In dichloromethane; toluene
4-[3-(5-Methyl-2-phenyl-4-oxazolyl)propionyl]bromobenzene

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

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

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

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

Conditions
ConditionsYield
silica gel In tetrahydrofuran; methanol; hexane; dichloromethane; water87%, >99%

112022-83-0Relevant articles and documents

Efficient synthesis of (R)-phenylephrine using a polymer-supported Corey-Bakshi-Shibata catalyst

Dai, Shuangxiong,Li, Guohua,Zhang, Wenbo,Zhang, Cuiyan,Song, Xiaoling,Huang, Di

, p. 740 - 743 (2017)

An efficient and mild synthetic route to (R)-phenylephrine hydrochloride using Corey-Bakshi-Shibata (CBS) catalyst was reported. In order to avoid a lengthy recovery process of the catalyst from homogeneous reaction, a polymer-supported CBS catalyst was prepared, and a preliminary attempt was made to achieve a continuous reduction on a laboratory scale, which contributes to synthesis of (R)-phenylephrine in a cost-effective way.

Process for the preparation of 1,3,2-oxazaborolidine compounds

-

Page/Page column 7, (2008/12/06)

A process is used for the preparation of 1,3,2-oxazaborolidine compounds. This process prepares compounds of formula (I) or (IA): in which: R1 is an alkyl or an aryl; and R2, R3, R4 and R5 are especially a hydrogen atom or an alkyl, wherein the following are reacted in two steps: a) a boric precursor compound with an acetal compound to give a boronate compound; and b) the boronate compound with an amino alcohol compound. This process avoids by-products and exhibits a very good stereospecificity.

Azabicycloalkane compounds

-

Page 30, (2008/06/13)

This invention provides compounds of formula I: wherein R1, R2, R3, R4, R5, R6 and R7 are as defined in the specification, or a pharmaceutically acceptable salt or solvate or stereoisomer thereof. The compounds of this invention possess both β2 adrenergic receptor agonist and muscarinic receptor antagonist activity. Such compounds are useful for treating pulmonary disorders, such as chronic obstructive pulmonary disease and asthma.

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