(R)-(-)-3-Quinuclidinol supplier

Name
(R)-(-)-3-Quinuclidinol
EINECS 246-857-6
CAS No. 25333-42-0
Article Data51
CAS DataBase
Density 1.13 g/cm₃
Solubility 100 g/100 mL
Melting Point 217-224 °C
Formula C₇H₁₃NO
Boiling Point 206.9 °C at 760 mmHg
Molecular Weight 127.186
Flash Point 97.7 °C
Transport Information UN 3263
Appearance White solid
Safety 45-36/37/39-26-16
Risk Codes 34-11
Molecular Structure
Hazard Symbols F, C
Synonyms 1-Azabicyclo[2.2.2]octan-3-ol,(R)-;3-Quinuclidinol, (-)- (8CI);(-)-3-Quinuclidinol;(3R)-1-Azabicyclo[2.2.2]octan-3-ol;(3R)-3-Quinuclidinol;(3R)-Quinuclidin-3-ol;(R)-(-)-1-Azabicyclo[2.2.2]octan-3-ol;(R)-1-Azabicyclo[2.2.2]octan-3-ol;(R)-3-Hydroxyquinuclidine;(R)-3-Quinuclidinol;(R)-3-Quinuclidol;R-Quinuclidin-3-ol;l-3-Quinuclidinol;
PSA 23.47000
LogP 0.01080

Synthetic route

: 3731-38-2
3-Quinuclidinone

: 25333-42-0
(R)-quinuclidin-3-ol

Conditions

Conditions	Yield
With potassium tert-butylate; hydrogen; RuCl2[(S,S)-xylskewphos] (dmf)n In ethanol at 30℃; under 7600.51 Torr; for 19h; Product distribution / selectivity;	100%
With trans-RuCl2((S)-BINAP)((R)-iphan); potassium tert-butylate; hydrogen In isopropyl alcohol at 25℃; under 38002.6 Torr; for 24h; optical yield given as %ee; enantioselective reaction;	99%
With potassium tert-butylate; hydrogen; RuBr2[(S,S)-xylskewphos](6-Me-pica) In ethanol at 30℃; under 7600.51 Torr; for 19h; Product distribution / selectivity;	95%

: (3R)-1-azabicyclo[2.2.2]octan-3-ol hydrochloride

: 25333-42-0
(R)-quinuclidin-3-ol

Conditions

Conditions	Yield
With sodium hydroxide In water at 20℃; for 0.166667h;	99%
With sodium hydroxide In water at 20℃; for 0.166667h;	99%
With sodium hydroxide In water at 20℃; for 0.166667h;	99%

: 1193-65-3
3-quinuclidinone hydrochloride

: 25333-42-0
(R)-quinuclidin-3-ol

Conditions

Conditions	Yield
With D-glucose In aq. phosphate buffer at 37℃; for 30h; pH=8; Concentration; Temperature; pH-value; Time;	93%
Multi-step reaction with 2 steps 1: sodium; ethanol 2: (1S)-2-oxo-bornane-10-sulfonic acid View Scheme
With R-DAIPEN; potassium tert-butylate; hydrogen; [RuCl(p-cymene)((R)-DM-SEGPHOS)]Cl In isopropyl alcohol at 30℃; under 22502.3 Torr; for 8h; Conversion of starting material;	n/a

: C7H13NO*C18H14O8

: 25333-42-0
(R)-quinuclidin-3-ol

Conditions

Conditions	Yield
With hydrogenchloride In water; ethyl acetate at 25 - 30℃; for 1h; pH=1 - 2; Resolution of racemate;	91%

: 854934-70-6
(3R)-1-azabicyclo[2.2.2]oct-3-yl benzoate (L)-tartrate

: 25333-42-0
(R)-quinuclidin-3-ol

Conditions

Conditions	Yield
With sodium hydroxide; water In methanol at 50℃; for 10h;	90%
With sodium hydroxide; water In methanol at 50℃; for 10h;	90%
With sodium hydroxide In methanol; water at 50℃; for 10h;	90%

: (R)-3-acetoxyquinuclidinium L-tartrate

: 25333-42-0
(R)-quinuclidin-3-ol

Conditions

Conditions	Yield
With sodium hydroxide In ethanol for 3h;	82.4%
With sodium hydroxide In water at 70℃; for 1h;	57.3%

: 59653-40-6
(+)-Aceclidine

: 25333-42-0
(R)-quinuclidin-3-ol

Conditions

Conditions	Yield
With sodium hydroxide at 50℃; for 1h;	80%

: 1619-34-7
3-quinuclidinol

: 25333-42-0
(R)-quinuclidin-3-ol

Conditions

Conditions	Yield
With camphor-10-sulfonic acid
Multi-step reaction with 3 steps 1: 90 percent / 4 h / Heating 3: 80 percent / 2.5N aq. NaOH / 1 h / 50 °C View Scheme
Multi-step reaction with 3 steps 1: 2 h / 20 °C 2: ethanol; water / 0.33 h / 50 °C 3: sodium hydroxide / water / 1 h / 70 °C View Scheme
Multi-step reaction with 3 steps 1: Reflux 2: ethanol / 7 h / 20 °C 3: sodium hydroxide / ethanol / 3 h View Scheme

: 3-Methoxymethoxy-1-aza-bicyclo[2.2.2]octane

A: 3684-26-2, 25333-42-0, 34583-34-1, 1619-34-7
(S)-quinuclidin-3-ol

B: 25333-42-0
(R)-quinuclidin-3-ol

Conditions

Conditions	Yield
With hydrogenchloride; water for 0.25h; Heating; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

: 174590-62-6
(R)-quinuclidin-3-yl benzoate

A: 65-85-0
benzoic acid

B: 25333-42-0
(R)-quinuclidin-3-ol

Conditions

Conditions	Yield
With horse serum butyrycholinesterase; water In phosphate buffer at 30℃; pH=7.4; Enzyme kinetics;

: 65732-89-0, 95074-03-6, 149836-59-9, 149884-95-7
quinuclidin-3-yl butyrate b

A: 3684-26-2, 25333-42-0, 34583-34-1, 1619-34-7
(S)-quinuclidin-3-ol

B: 25333-42-0
(R)-quinuclidin-3-ol

C: (S)-quinuclidin-3-yl butyrate

D: 65732-89-0
(R)-quinuclidin-3-yl butyrate

Conditions

Conditions	Yield
With Aspergillus melleus protease In phosphate buffer at 25℃; for 16h; pH=7.5; Title compound not separated from byproducts;
With Bacillus licheniformis subtilisin; water at 20℃; for 16h; Enzymatic reaction; optical yield given as %ee; enantioselective reaction;

...Expand

: isobutyric acid 1-aza-bicyclo[2.2.2]oct-3-yl ester

A: 3684-26-2, 25333-42-0, 34583-34-1, 1619-34-7
(S)-quinuclidin-3-ol

B: 25333-42-0
(R)-quinuclidin-3-ol

C: Isobutyric acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl) ester

D: Isobutyric acid (S)-(1-aza-bicyclo[2.2.2]oct-3-yl) ester

Conditions

Conditions	Yield
With Aspergillus melleus protease In phosphate buffer at 25℃; for 16h; pH=7.5; Title compound not separated from byproducts;

...Expand

: 65732-89-0
(R)-quinuclidin-3-yl butyrate

: 25333-42-0
(R)-quinuclidin-3-ol

Conditions

Conditions	Yield
With sodium carbonate In methanol at 65℃; for 16h;	5.3 g
With water; sodium hydroxide In methanol optical yield given as %ee;

: pentanoic acid 1-aza-bicyclo[2.2.2]oct-3-yl ester

A: 3684-26-2, 25333-42-0, 34583-34-1, 1619-34-7
(S)-quinuclidin-3-ol

B: 25333-42-0
(R)-quinuclidin-3-ol

C: Pentanoic acid (S)-(1-aza-bicyclo[2.2.2]oct-3-yl) ester

D: Pentanoic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl) ester

Conditions

Conditions	Yield
With Aspergillus melleus protease In phosphate buffer at 25℃; for 16h; pH=7.5; Title compound not separated from byproducts;

...Expand

: hexanoic acid 1-aza-bicyclo[2.2.2]oct-3-yl ester

A: 3684-26-2, 25333-42-0, 34583-34-1, 1619-34-7
(S)-quinuclidin-3-ol

B: 25333-42-0
(R)-quinuclidin-3-ol

C: Hexanoic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl) ester

Conditions

Conditions	Yield
With Aspergillus melleus protease In phosphate buffer at 25℃; for 16h; pH=7.5; Title compound not separated from byproducts;

...Expand

: octanoic acid 1-aza-bicyclo[2.2.2]oct-3-yl ester

A: 3684-26-2, 25333-42-0, 34583-34-1, 1619-34-7
(S)-quinuclidin-3-ol

B: 25333-42-0
(R)-quinuclidin-3-ol

C: Octanoic acid (S)-(1-aza-bicyclo[2.2.2]oct-3-yl) ester

D: Octanoic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl) ester

Conditions

Conditions	Yield
With Aspergillus melleus protease In phosphate buffer at 25℃; for 16h; pH=7.5; Title compound not separated from byproducts;

...Expand

: quinuclidin-3-yl butyrate butyric acid salt

A: 3684-26-2, 25333-42-0, 34583-34-1, 1619-34-7
(S)-quinuclidin-3-ol

B: 25333-42-0
(R)-quinuclidin-3-ol

C: 65732-89-0
(R)-quinuclidin-3-yl butyrate

Conditions

Conditions	Yield
With calcium hydroxide; Aspergillus melleus protease In water at 25℃; for 24h; Title compound not separated from byproducts;

...Expand

: (R)-3-quinuclidinol acetate (2S,3S)-tartaric acid salt

: 25333-42-0
(R)-quinuclidin-3-ol

Conditions

Conditions	Yield
With sodium hydroxide at 75℃; for 2h;

: 1619-34-7
3-quinuclidinol

A: 3684-26-2, 25333-42-0, 34583-34-1, 1619-34-7
(S)-quinuclidin-3-ol

B: 25333-42-0
(R)-quinuclidin-3-ol

Conditions

Conditions	Yield
Stage #1: 3-quinuclidinol With acetic anhydride at 160℃; for 3h; Stage #2: With sodium hydroxide at 75℃; for 2h;
Resolution of racemate;

: 827-61-2, 59653-40-6, 59653-42-8, 72353-53-8
3-acetoxyquinuclidine

: 25333-42-0
(R)-quinuclidin-3-ol

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 2: 80 percent / 2.5N aq. NaOH / 1 h / 50 °C View Scheme
Multi-step reaction with 2 steps 1: ethanol; water / 0.33 h / 50 °C 2: sodium hydroxide / water / 1 h / 70 °C View Scheme

: 1838-39-7
ethyl N-ethoxycarbonylmethyl-4-piperidinecarboxylate

: 25333-42-0
(R)-quinuclidin-3-ol

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: potassium; toluene / anschliessend mit konz. Salzsaeure 2: lithium alanate; diethyl ether 3: (1S)-2-oxo-bornane-10-sulfonic acid View Scheme
Multi-step reaction with 6 steps 1.1: potassium tert-butylate / toluene / 4.5 h / Reflux; Inert atmosphere 2.1: Reflux 2.2: 20 °C 3.1: sodium hydroxide; water / 0.5 h / -5 - 0 °C 3.2: 1.5 h 4.1: 2 h / 20 °C 5.1: ethanol; water / 0.33 h / 50 °C 6.1: sodium hydroxide / water / 1 h / 70 °C View Scheme

: 3731-38-2
3-Quinuclidinone

A: 3684-26-2, 25333-42-0, 34583-34-1, 1619-34-7
(S)-quinuclidin-3-ol

B: 25333-42-0
(R)-quinuclidin-3-ol

Conditions

Conditions	Yield
With hydrogen; (S)-1-[(R)-1',2-bis (diphenylphosphino) ferrocenyl] ethanol; 1,5-cyclooctadienerhodium (I) chloride dimer; (R,R)-1,2-diphenylethylenediamine In ethanol at 30℃; under 26252.6 Torr; for 16h; Product distribution / selectivity;	A n/a B n/a
With hydrogen; (S)-(-)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl; 1,5-cyclooctadienerhodium (I) chloride dimer; (R,R)-1,2-diphenylethylenediamine In tetrahydrofuran; ethanol at 30℃; under 26252.6 Torr; for 20h; Product distribution / selectivity;	A n/a B n/a
With hydrogen; (S)-(-)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl; 1,5-cyclooctadienerhodium (I) chloride dimer In tetrahydrofuran; ethanol at 30℃; under 26252.6 Torr; for 20h; Product distribution / selectivity;	A n/a B n/a

: 34286-16-3
2-ethoxycarbonyl-3-quinuclidinone

: 25333-42-0
(R)-quinuclidin-3-ol

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: Reflux 1.2: 20 °C 2.1: sodium hydroxide; water / 0.5 h / -5 - 0 °C 2.2: 1.5 h 3.1: 2 h / 20 °C 4.1: ethanol; water / 0.33 h / 50 °C 5.1: sodium hydroxide / water / 1 h / 70 °C View Scheme

: 3-acetoxyquinuclidinine acetate

: 25333-42-0
(R)-quinuclidin-3-ol

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: ethanol / 7 h / 20 °C 2: sodium hydroxide / ethanol / 3 h View Scheme

: 860169-77-3
ethyl 6-((3S,4R)-4-(dibenzylamino)-3-methoxypiperidin-1-yl)hexanoate

: 25333-42-0
(R)-quinuclidin-3-ol

: 860169-80-8
(R)-quinuclidin-3-yl 6-((3S,4R)-4-(dibenzylamino)-3-methoxypiperidin-1-yl)hexanoate

Conditions

Conditions	Yield
With titanium(IV) tetraethanolate In toluene at 0 - 90℃; for 18h; Product distribution / selectivity; Heating / reflux;	100%
With titanium(IV) isopropylate In toluene at 160℃; Product distribution / selectivity;
With titanium(IV) tetraethanolate In toluene at 90℃; Dean-Stark apparatus;

: 25333-42-0
(R)-quinuclidin-3-ol

: 66548-50-3
3-(p-bromophenyl)-6-chloropyridazine

: 855738-48-6
(3R)-3-[6-(4-bromo-phenyl)-pyridazin-3-yloxy]-1-aza-bicyclo[2.2.2]octane

Conditions

Conditions	Yield
With potassium tert-butylate In tetrahydrofuran at 20℃; for 10h;	100%
With potassium tert-butylate In tetrahydrofuran

: 637-59-2
1-Bromo-3-phenylpropane

: 25333-42-0
(R)-quinuclidin-3-ol

: (3R)-3-hydroxy-1-(3-phenylpropyl)-1-azoniabicyclo[2.2.2]octane bromide

Conditions

Conditions	Yield
In tetrahydrofuran for 7h; Heating / reflux;	100%

: 54149-17-6
1-bromo-2-(2-methoxyethoxy)ethane

: 25333-42-0
(R)-quinuclidin-3-ol

: (3R)-3-hydroxy-1-[2-(2-methoxyethoxy)ethyl]-1-azoniabicyclo[2.2.2]octane bromide

Conditions

Conditions	Yield
In tetrahydrofuran for 16h; Heating / reflux;	100%

: 1233329-71-9
(2-methoxy-phenylamino)-phenyl-acetic acid hydrochloride

: 25333-42-0
(R)-quinuclidin-3-ol

: 1233326-93-6
(2-methoxy-phenylamino)-phenyl-acetic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl) ester

Conditions

Conditions	Yield
Stage #1: (2-methoxy-phenylamino)-phenyl-acetic acid hydrochloride With benzotriazol-1-ol In tetrahydrofuran for 0.166667h; Stage #2: (R)-quinuclidin-3-ol In tetrahydrofuran at 20℃; for 16h;	100%

: 1233329-72-0
phenyl-o-methyl phenylamino-acetic acid hydrochloride

: 25333-42-0
(R)-quinuclidin-3-ol

: 1233326-94-7
phenyl-o-methylphenylamino-acetic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl) ester

Conditions

Conditions	Yield
With benzotriazol-1-ol In tetrahydrofuran at 20℃; for 16h;	100%
With benzotriazol-1-ol In tetrahydrofuran at 20℃; for 16h;	100%

: 1233329-78-6
(3-acetylamino-phenylamino)-phenyl-acetic acid hydrochloride

: 25333-42-0
(R)-quinuclidin-3-ol

: 1233326-97-0
(3-acetylamino-phenylamino)-phenyl-acetic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl) ester

Conditions

Conditions	Yield
With benzotriazol-1-ol In tetrahydrofuran at 20℃; for 16h;	100%

: 1233329-80-0
(3-fluoro-4-methyl-phenylamino)-phenyl-acetic acid hydrochloride

: 25333-42-0
(R)-quinuclidin-3-ol

: 1233326-99-2
(3-fluoro-4-methyl-phenylamino)-phenyl-acetic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl) ester

Conditions

Conditions	Yield
With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃;	100%

: 1233329-83-3
(3-methylsulfanyl-phenylamino)-phenyl-acetic acid hydrochloride

: 25333-42-0
(R)-quinuclidin-3-ol

: 1233327-00-8
(3-methylsulfanyl-phenylamino)-phenyl-acetic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl) ester

Conditions

Conditions	Yield
With benzotriazol-1-ol In tetrahydrofuran at 20℃; for 16h;	100%

: 1233329-93-5
(2-acetyl-phenylamino)-phenyl-acetic acid hydrochloride

: 25333-42-0
(R)-quinuclidin-3-ol

: 1233327-06-4
(2-acetyl-phenylamino)-phenyl-acetic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl) ester

Conditions

Conditions	Yield
With benzotriazol-1-ol In tetrahydrofuran at 20℃;	100%

: 1352565-74-2
2-(3-(methylcarbamoyl)phenylamino)-2-phenylacetic acid hydrochloride

: 25333-42-0
(R)-quinuclidin-3-ol

: 1233326-98-1
(3-methylcarbamoyl-phenylamino)-phenyl-acetic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl) ester

Conditions

Conditions	Yield
With benzotriazol-1-ol In tetrahydrofuran at 20℃; for 16h;	100%

: 142121-94-6
2-(tert-butoxycarbonylamino)-2-(3-fluorophenyl)acetic acid

: 25333-42-0
(R)-quinuclidin-3-ol

: 1379513-70-8
(R)-quinuclidin-3-yl 2-(tert-butoxycarbonylamino)-2-(3-fluorophenyl)acetate

Conditions

Conditions	Yield
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃; for 15h;	100%
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃;	100%

: 161330-30-9
2-((tert-butoxycarbonyl)amino)-2-(2-fluorophenyl)acetic acid

: 25333-42-0
(R)-quinuclidin-3-ol

: 1379513-72-0
(R)-quinuclidin-3-yl 2-(tert-butoxycarbonylamino)-2-(2-fluorophenyl)acetate

Conditions

Conditions	Yield
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃; for 15h;	100%
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃;	100%

: 5781-53-3
monomethyl oxalyl chloride

: 25333-42-0
(R)-quinuclidin-3-ol

: C10H15NO4*ClH

Conditions

Conditions	Yield
In dichloromethane at 0 - 20℃; for 12h; Inert atmosphere;	99%

: 25333-42-0
(R)-quinuclidin-3-ol

: 503-38-8
trichloromethyl chloroformate

: (R)-quinuclidin-3-yl carbonochloridate hydrochloride

Conditions

Conditions	Yield
In acetonitrile at 0 - 20℃; for 17h;	98%
In acetonitrile at 0 - 20℃; for 17h;	98%
In acetonitrile at 0 - 20℃; for 17h;	98%

: 25333-42-0
(R)-quinuclidin-3-ol

: 503-38-8
trichloromethyl chloroformate

: (R)-quinuclidin-3-yl carbonochioridate

Conditions

Conditions	Yield
In acetonitrile at 0 - 20℃; for 17h;	98%

: 25333-42-0
(R)-quinuclidin-3-ol

: 503-38-8
trichloromethyl chloroformate

: (R)-quinuclidin-3-yl carbonochloridate hydrochloride

Conditions

Conditions	Yield
In acetonitrile at 0 - 20℃; for 17h;	98%
In acetonitrile at 0 - 20℃; for 17h;	98%
In acetonitrile at 0 - 20℃; for 17h;	98%

: 71066-00-7
2-((tert-butoxycarbonyl)amino)-2,3-dihydro-1H-indene-2-carboxylic acid

: 25333-42-0
(R)-quinuclidin-3-ol

: (R)-quinuclidin-3-yl 2-amino-2,3-dihydro-1H-indene-2-carboxylate dihydrochloride

Conditions

Conditions	Yield
Stage #1: 2-((tert-butoxycarbonyl)amino)-2,3-dihydro-1H-indene-2-carboxylic acid With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 50℃; for 0.666667h; Stage #2: (R)-quinuclidin-3-ol In N,N-dimethyl-formamide at 50℃; for 120h; Stage #3: With hydrogenchloride In 1,4-dioxane at 20℃; for 3h;	98%

: 2900-27-8, 3601-66-9, 14675-97-9, 33125-05-2
2-(tert-butoxycarbonylamino)-2-phenylacetic acid

: 25333-42-0
(R)-quinuclidin-3-ol

: 1233329-64-0
(1-methyl-4-piperidyl) 2-(tert-butoxycarbonylamino)-2-phenylacetate

Conditions

Conditions	Yield
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃; for 16h;	97%
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃; for 20h;	77%
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃;	58.5%
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃;	58.5%

: C34H29NO2P(1+)*Cl(1-)

: 25333-42-0
(R)-quinuclidin-3-ol

: 242478-37-1
solifenacin

Conditions

Conditions	Yield
In toluene at 60 - 70℃; Temperature;	96.8%

: 611-73-4
Benzoylformic acid

: 25333-42-0
(R)-quinuclidin-3-ol

: 141831-51-8
(3R)-1-azabicyclo[2.2.2]oct-3-yl oxo(phenyl)acetate

Conditions

Conditions	Yield
Stage #1: Benzoylformic acid With oxalyl dichloride; N,N-dimethyl-formamide In chloroform at 0 - 20℃; Stage #2: (R)-quinuclidin-3-ol In chloroform at 20℃;	96%

: 180468-42-2
(S)-N-carboxylic acid ethyl ester-1-phenyl-1,2,3,4-tetrahydroisoquinoline

: 25333-42-0
(R)-quinuclidin-3-ol

: 242478-37-1
solifenacin

Conditions

Conditions	Yield
With sodium hydride; 1-butyl-3-methylimidazolium Tetrafluoroborate In N,N-dimethyl-formamide at 100℃; for 6h; Temperature; Concentration;	95.1%
With sodium hydride In toluene for 3h; Heating;	89%
Stage #1: (R)-quinuclidin-3-ol With sodium hydride In toluene; mineral oil at 0℃; for 0.25h; Inert atmosphere; Stage #2: (S)-N-carboxylic acid ethyl ester-1-phenyl-1,2,3,4-tetrahydroisoquinoline In toluene; mineral oil at 130℃; for 8h; Inert atmosphere; Dean-Stark;	88%

: 17337-13-2
[1,1'-biphenyl]-2-yl-isocyanate

: 25333-42-0
(R)-quinuclidin-3-ol

: 763067-35-2
(R)-quinuclidin-3-yl biphenyl-2-ylcarbamate

Conditions

Conditions	Yield
at 70℃; neat (no solvent);	95%
In N,N-dimethyl-formamide; toluene at 110℃; for 3.6h; Yield given;

: 93-97-0
benzoic acid anhydride

: 25333-42-0
(R)-quinuclidin-3-ol

: 174590-62-6
(R)-quinuclidin-3-yl benzoate

Conditions

Conditions	Yield
at 130℃; for 1h;	95%
Stage #1: benzoic acid anhydride; (R)-quinuclidin-3-ol at 70℃; for 0.166667h; Stage #2: With hydrogenchloride; water In tert-butyl methyl ether Stage #3: With water; sodium hydroxide pH=13; optical yield given as %ee;

: 2094-99-7
1-(1-isocyanato-1-methylethyl)-3-(1-methylethenyl)benzene

: 25333-42-0
(R)-quinuclidin-3-ol

: 1401089-70-0
(R)-quinuclidin-3-yl 2-(3-(prop-1-en-2-yl)phenyl)propan-2-ylcarbamate

Conditions

Conditions	Yield
With sodium hydride In tetrahydrofuran; mineral oil at 20℃; for 0.75h;	95%

: 865378-28-5
methyl 2,2-di-2-thienylpropanoate

: 25333-42-0
(R)-quinuclidin-3-ol

: (3R)-1-azabicyclo[2.2.2]oct-3-yl 2,2-di-2-thienylpropanoate

Conditions

Conditions	Yield
With sodium hydride In toluene for 1.66667h; Heating / reflux;	94.07%
With sodium hydride In toluene; mineral oil for 1.5h; Reflux;	94.1%

: 60729-82-0
α-(2-oxo-1-pyrrolidinyl)phenylacetic acid

: 25333-42-0
(R)-quinuclidin-3-ol

: 1446308-25-3
(R)-quinuclidin-3-yl 2-(2-oxopyrrolidin-1-yl)-2-phenylacetate

Conditions

Conditions	Yield
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃; for 24h;	93%
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃; for 24h;	93%

(R)-(-)-3-Quinuclidinol Chemical Properties

Product Name: (R)-(-)-3-Quinuclidinol (CAS NO.25333-42-0)

Molecular Formula: C₇H₁₃NO
Molecular Weight: 127.18g/mol
Mol File: 25333-42-0.mol
EINECS: 246-857-6
Appearance: White Solid
Melting Point: 217-224 °C
Boiling point: 206.9 °C at 760 mmHg
Storage Temperature: Flammables area
Flash Point: 97.7 °C
Density: 1.13 g/cm³
Water Solubility: 100 g/100 mL
Index of Refraction: 1.549
Molar Refractivity: 35.73 cm³
Molar Volume: 112.2 cm³
Surface Tension: 44.8 dyne/cm
Enthalpy of Vaporization: 51.55 kJ/mol
Vapour Pressure: 0.0545 mmHg at 25°C
XLogP3-AA: 0.2
H-Bond Donor: 1
H-Bond Acceptor: 2
Structure Descriptors of (R)-(-)-3-Quinuclidinol (CAS NO.25333-42-0):
IUPAC Name: (8R)-1-azabicyclo[2.2.2]octan-8-ol
Canonical SMILES: C1CN2CCC1C(C2)O
Isomeric SMILES: C1CN2CCC1[C@H](C2)O
InChI: InChI=1S/C7H13NO/c9-7-5-8-3-1-6(7)2-4-8/h6-7,9H,1-5H2/t7-/m0/s1
InChIKey: IVLICPVPXWEGCA-ZETCQYMHSA-N
Product Categories: Chiral Reagents; Heterocycles; Intermediates & Fine Chemicals; Pharmaceuticals

(R)-(-)-3-Quinuclidinol Safety Profile

Safety Information of (R)-(-)-3-Quinuclidinol (CAS NO.25333-42-0):
Hazard Codes: C Corrosive ,F
Risk Statements: 34-11
R34:Causes burns.
R11:Highly flammable.
Safety Statements: 45-36/37/39-26-16
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S16:Keep away from sources of ignition.
RIDADR: 3263

(R)-(-)-3-Quinuclidinol Specification

(R)-(-)-3-Quinuclidinol , its CAS NO. is 25333-42-0, the synonym is (R)-Quinuclidin-3-ol .

Product Name

(R)-(-)-3-Quinuclidinol

Synthetic route

(R)-(-)-3-Quinuclidinol Chemical Properties

(R)-(-)-3-Quinuclidinol Safety Profile

(R)-(-)-3-Quinuclidinol Specification

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