1-Azabicyclo[2.2.2]octane-3-carboxylicacid, ethyl ester supplier

Name
ETHYL 3-QUINUCLIDINECARBOXYLATE
EINECS 604-604-1
CAS No. 6238-33-1
Density 1.09 g/cm³
Solubility
Melting Point
Formula C₁₀H₁₇NO₂
Boiling Point 240.8 °C at 760 mmHg
Molecular Weight 183.25
Flash Point 89.6 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 3-Quinuclidinecarboxylicacid, ethyl ester (7CI,8CI);3-Carbethoxyquinuclidine;Ethyl 3-quinuclidinecarboxylate;
PSA 29.54000
LogP 0.82920

Synthetic route

: 6238-33-1
3-quinuclidinecarboxylic acid ethyl ester

: 75208-40-1
quinuclidine-3-carboxylic acid

Conditions

Conditions	Yield
With water for 3h; Heating;	100%
With hydrogenchloride for 5h; Heating;
With hydrogenchloride Heating;

: 6238-33-1
3-quinuclidinecarboxylic acid ethyl ester

: 5176-22-7
3-hydroxymethyl-1-azabicyclo[2.2.2]octane

Conditions

Conditions	Yield
With lithium aluminium tetrahydride In diethyl ether for 2h; Heating;	91%

: 6238-33-1
3-quinuclidinecarboxylic acid ethyl ester

: 6238-34-2
1-azabicyclo<2.2.2>octane-3-carboxylic acid hydrochloride

Conditions

Conditions	Yield
With hydrogenchloride for 4h; Heating;	80%

: 188290-36-0
thiophene

: 108-86-1
bromobenzene

: 6238-33-1
3-quinuclidinecarboxylic acid ethyl ester

: 591-51-5
phenyllithium

: 57734-76-6
di(2-thienyl)(3-quinuclidyl)carbinol hydrochloride

Conditions

Conditions	Yield
Stage #1: bromobenzene With lithium In diethyl ether for 1h; Metallation; Heating; Stage #2: thiophene; phenyllithium at 25℃; for 0.75h; Addition; Stage #3: 3-quinuclidinecarboxylic acid ethyl ester In diethyl ether at -10 - -5℃; for 0.5h; Condensation;	67.4%

...Expand

: 188290-36-0
thiophene

: 108-86-1
bromobenzene

: 6238-33-1
3-quinuclidinecarboxylic acid ethyl ester

: 57734-76-6
di(2-thienyl)(3-quinuclidyl)carbinol hydrochloride

Conditions

Conditions	Yield
Stage #1: bromobenzene With lithium In diethyl ether for 1h; Metallation; Heating; Stage #2: thiophene In diethyl ether at 20℃; for 1.5h; Metallation; Stage #3: 3-quinuclidinecarboxylic acid ethyl ester With hydrogenchloride In diethyl ether; water at -10 - 20℃; for 1.5h; Addition;	67%

...Expand

: 126145-44-6
N-Hydroxy-2-(2-oxo-pyrrolidin-1-yl)-acetamidine

: 6238-33-1
3-quinuclidinecarboxylic acid ethyl ester

: 1-((5-(1-azabicyclo[2.2.2]octan-3-yl)-1,2,4-oxadiazol-3-yl)methyl)pyrrolidin-2-one

Conditions

Conditions	Yield
With sodium hydride In tetrahydrofuran; mineral oil Inert atmosphere; Schlenk technique; Molecular sieve; Reflux;	47%

: 1003-09-4
2-bromothiophene

: 6238-33-1
3-quinuclidinecarboxylic acid ethyl ester

: 60697-86-1
(3-quinuclidyl)(2-thienyl)ketone

Conditions

Conditions	Yield
(i) Mg, Et2O, (ii) /BRN= 473684/; Multistep reaction;

: 1003-09-4
2-bromothiophene

: 6238-33-1
3-quinuclidinecarboxylic acid ethyl ester

: 57734-75-5
(3-Quinuclidyl) di(2-thienyl) carbinol

Conditions

Conditions	Yield
(i) Mg, Et2O, (ii) /BRN= 473684/; Multistep reaction;

: 6238-33-1
3-quinuclidinecarboxylic acid ethyl ester

: 5713-61-1
thiophen-2-yl magnesium bromide

: 60697-86-1
(3-quinuclidyl)(2-thienyl)ketone

Conditions

Conditions	Yield
In diethyl ether

: 6238-33-1
3-quinuclidinecarboxylic acid ethyl ester

: 5713-61-1
thiophen-2-yl magnesium bromide

: 57734-75-5
(3-Quinuclidyl) di(2-thienyl) carbinol

Conditions

Conditions	Yield
In diethyl ether

: 110-00-9
furan

: 6238-33-1
3-quinuclidinecarboxylic acid ethyl ester

: 132668-72-5
(3-Quinuclidyl) di(2-furyl) carbinol

Conditions

Conditions	Yield
With 1-bromo-butane; lithium 1.) ether, 20-25 deg C, 30 min; reflux, 1 h, 2.) ether, 4 deg C, 15 h; Yield given. Multistep reaction;

: 6238-33-1
3-quinuclidinecarboxylic acid ethyl ester

: 83598-29-2
(1-azabicyclo[2.2.2]octan-3-yl)carbonyl chloride

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: aq. HCl / Heating 2: SOCl2 View Scheme
Multi-step reaction with 2 steps 1: 8M aq. HCl / 5 h / Heating 2: SOCl2 / CH2Cl2 / 4 h / Heating View Scheme

: 6238-33-1
3-quinuclidinecarboxylic acid ethyl ester

: 133366-37-7
N-methoxy-N-methyl-1-azabicyclo<2.2.2>octane-3-formamide

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: aq. HCl / Heating 2: SOCl2 3: Et3N View Scheme

: 6238-33-1
3-quinuclidinecarboxylic acid ethyl ester

: 3-benzo[b]thiophen-2-ylmethyl-1-aza-bicyclo[2.2.2]octane

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: aq. HCl / Heating 2: SOCl2 3: Et3N 4: 42 percent / -78 °C 5: NaBH4 6: NaI; TMSCl / acetonitrile View Scheme

: 6238-33-1
3-quinuclidinecarboxylic acid ethyl ester

: (1-aza-bicyclo[2.2.2]oct-3-yl)-benzo[b]thiophen-2-yl-methanol

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: aq. HCl / Heating 2: SOCl2 3: Et3N 4: 42 percent / -78 °C 5: NaBH4 View Scheme

: 6238-33-1
3-quinuclidinecarboxylic acid ethyl ester

: 392287-48-8
(1-aza-bicyclo[2.2.2]oct-3-yl)-benzo[b]thiophen-2-yl-methanone

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: aq. HCl / Heating 2: SOCl2 3: Et3N 4: 42 percent / -78 °C View Scheme

: 6238-33-1
3-quinuclidinecarboxylic acid ethyl ester

: 149156-47-8
N-methoxy-1-azabicyclo[2.2.2]octane-3-carboxamide

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 8M aq. HCl / 5 h / Heating 2: SOCl2 / CH2Cl2 / 4 h / Heating 3: 92 percent / pyridine / acetonitrile; CHCl3 / 2 h / Ambient temperature View Scheme

: 6238-33-1
3-quinuclidinecarboxylic acid ethyl ester

: 155613-14-2
(Z)-N-methoxy-1-azabicyclo[2.2.2]octane-3-carboximidoyl chloride

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 8M aq. HCl / 5 h / Heating 2: SOCl2 / CH2Cl2 / 4 h / Heating 3: 92 percent / pyridine / acetonitrile; CHCl3 / 2 h / Ambient temperature 4: 57 percent / CCl4, Ph3P / acetonitrile / 0.33 h / Heating View Scheme

: 6238-33-1
3-quinuclidinecarboxylic acid ethyl ester

: [R,S]-α-(methoxyimino)-α-(1-azabicyclo[2.2.2]oct-3-yl)acetonitrile

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 8M aq. HCl / 5 h / Heating 2: SOCl2 / CH2Cl2 / 4 h / Heating 3: 92 percent / pyridine / acetonitrile; CHCl3 / 2 h / Ambient temperature 4: 57 percent / CCl4, Ph3P / acetonitrile / 0.33 h / Heating 5: dimethylsulfoxide / 7 h / 95 °C View Scheme

: 6238-33-1
3-quinuclidinecarboxylic acid ethyl ester

: 151433-82-8
(+/-) SKB20206

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 8M aq. HCl / 5 h / Heating 2: SOCl2 / CH2Cl2 / 4 h / Heating 3: 92 percent / pyridine / acetonitrile; CHCl3 / 2 h / Ambient temperature 4: 57 percent / CCl4, Ph3P / acetonitrile / 0.33 h / Heating 5: dimethylsulfoxide / 7 h / 95 °C View Scheme

: 6238-33-1
3-quinuclidinecarboxylic acid ethyl ester

: sabcomeline

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: 8M aq. HCl / 5 h / Heating 2: SOCl2 / CH2Cl2 / 4 h / Heating 3: 92 percent / pyridine / acetonitrile; CHCl3 / 2 h / Ambient temperature 4: 57 percent / CCl4, Ph3P / acetonitrile / 0.33 h / Heating 5: dimethylsulfoxide / 7 h / 95 °C View Scheme

: 6238-33-1
3-quinuclidinecarboxylic acid ethyl ester

: (S)-1-Aza-bicyclo[2.2.2]oct-3-yl-[(Z)-methoxyimino]-acetonitrile

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: 8M aq. HCl / 5 h / Heating 2: SOCl2 / CH2Cl2 / 4 h / Heating 3: 92 percent / pyridine / acetonitrile; CHCl3 / 2 h / Ambient temperature 4: 57 percent / CCl4, Ph3P / acetonitrile / 0.33 h / Heating 5: dimethylsulfoxide / 7 h / 95 °C View Scheme

: 6238-33-1
3-quinuclidinecarboxylic acid ethyl ester

: (Z)-N-methoxy-1-azabicyclo[2.2.2]octane-3-carboximidoyl fluoride

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 8M aq. HCl / 5 h / Heating 2: SOCl2 / CH2Cl2 / 4 h / Heating 3: 92 percent / pyridine / acetonitrile; CHCl3 / 2 h / Ambient temperature 4: 57 percent / CCl4, Ph3P / acetonitrile / 0.33 h / Heating 5: CsF/CaF2 / dimethylformamide / 120 h / 145 °C View Scheme

: 6238-33-1
3-quinuclidinecarboxylic acid ethyl ester

: 134580-20-4
1,3-dimethyl-4-amino-5-(quinuclid-3-ylcarboxamin)uracil

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 80 percent / conc. HCl / 4 h / Heating 2: SOCl2 / 4 h / 75 - 80 °C 3: 40 percent / Et3N / CHCl3 / 2 h / Ambient temperature View Scheme

: 6238-33-1
3-quinuclidinecarboxylic acid ethyl ester

: 66073-50-5
quinuclidine-3-carboxylic acid chloride hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 80 percent / conc. HCl / 4 h / Heating 2: SOCl2 / 4 h / 75 - 80 °C View Scheme

: 6238-33-1
3-quinuclidinecarboxylic acid ethyl ester

: 134580-19-1
1,3-dimethyl-8-(quinuclid-3-yl)xanthine

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 80 percent / conc. HCl / 4 h / Heating 2: SOCl2 / 4 h / 75 - 80 °C 3: 40 percent / Et3N / CHCl3 / 2 h / Ambient temperature 4: 39 percent / 0.25 h / 240 °C View Scheme

: 6238-33-1
3-quinuclidinecarboxylic acid ethyl ester

: 62732-41-6, 102723-02-4
(1-aza-bicyclo[2.2.2]oct-3-yl)-thiophen-2-yl-methanol

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: diethyl ether 2: LiAlH4 / benzene; diethyl ether View Scheme

: 6238-33-1
3-quinuclidinecarboxylic acid ethyl ester

: 60698-05-7
3-

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: (i) Mg, Et2O, (ii) /BRN= 473684/ 2: HCO2H / 0.5 h / Heating View Scheme

1-Azabicyclo[2.2.2]octane-3-carboxylicacid, ethyl ester Specification

The 1-Azabicyclo[2. 2. 2]octane-3-carboxylicacid, ethyl ester, with the CAS registry number of 6238-33-1, is also known as 3-Carbethoxyquinuclidine. It belongs to the product category of Quinuclidine Derivatives. This chemical's molecular formula is C₁₀H₁₇NO₂ and molecular weight is 183.25. What's more, its systematic name is called Ethyl 1-azabicyclo[2. 2. 2]octane-3-carboxylate.

Physical properties about 1-Azabicyclo[2. 2. 2]octane-3-carboxylicacid, ethyl ester are: (1)ACD/LogP: 1.38; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -1.65; (4)ACD/LogD (pH 7.4): -0.57; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 1.49; (9)#H bond acceptors: 3; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 3; (12)Polar Surface Area: 29.54 Å²; (13)Index of Refraction: 1.507; (14)Molar Refractivity: 49.95 cm³; (15)Molar Volume: 167.6 cm³; (16)Polarizability: 19.8×10^-24 cm³; (17)Surface Tension: 39 dyne/cm; (18)Density: 1.09 g/cm³; (19)Flash Point: 89.6 °C; (20)Enthalpy of Vaporization: 47.77 kJ/mol; (21)Boiling Point: 240.8 °C at 760 mmHg; (22)Vapour Pressure: 0.0373 mmHg at 25 °C.

Uses: it is used to produce other chemicals. For example, it is used to produce Quiniuclidin-3-yl-methanol. The reaction needs reagent LiAlH₄ and solvent Diethyl ether. Other condition of this reaction is reaction time of 2 hours at heating. The yield is about 91 %.

You can still convert the following datas into molecular structure:
(1) SMILES: O=C(OCC)C1CN2CCC1CC2
(2) InChI: InChI=1/C10H17NO2/c1-2-13-10(12)9-7-11-5-3-8(9)4-6-11/h8-9H,2-7H2,1H3
(3) InChIKey: ZNYZKXCVJJQSEU-UHFFFAOYAG

Product Name

ETHYL 3-QUINUCLIDINECARBOXYLATE

Synthetic route

1-Azabicyclo[2.2.2]octane-3-carboxylicacid, ethyl ester Specification

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