6238-33-1

Basic information

• Product Name: ETHYL 3-QUINUCLIDINECARBOXYLATE
• Synonyms: 3-CARBETHOXYQUINUCLIDINE;1-AZABICYCLO[2.2.2]OCTAN-3-ETHYLCARBOXYLATE;ETHYL 3-QUINUCLIDINECARBOXYLATE;3-CARBETOXYQUINUCLIDINE;Ethyl quinuclidine-4-carboxylate;3-Quinuclidinecarboxylic acid ethyl ester
• CAS NO: 6238-33-1
• Molecular Formula: C₁₀H₁₇NO₂
• Molecular Weight: 183.25
• EINECS: 604-604-1
• Product Categories: Quinuclidine derivatives
• Mol File: 6238-33-1.mol
• Article Data: 0

Chemical Properties

• Boiling Point: 123-124℃ (15 Torr)
• Flash Point: 89.6 °C
• Appearance: /
• Density: 1.09 g/cm³
• Vapor Pressure: 4.69E-13mmHg at 25°C
• Refractive Index: 1.726
• PKA: 9.38±0.33(Predicted)
• CAS DataBase Reference: ETHYL 3-QUINUCLIDINECARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: ETHYL 3-QUINUCLIDINECARBOXYLATE(6238-33-1)
• EPA Substance Registry System: ETHYL 3-QUINUCLIDINECARBOXYLATE(6238-33-1)

Safety Data

• Hazardous Substances Data: 6238-33-1(Hazardous Substances Data)

Usage

General Description

ETHYL 3-QUINUCLIDINECARBOXYLATE is a chemical compound with the molecular formula C13H19NO2. It belongs to the class of organic compounds known as esters and is used in organic synthesis and pharmaceutical research. ETHYL 3-QUINUCLIDINECARBOXYLATE is derived from quinuclidine, an organic compound used as a catalyst in organic reactions. ETHYL 3-QUINUCLIDINECARBOXYLATE is a colorless liquid that is soluble in organic solvents. It has potential applications in the development of pharmaceutical drugs and can be used as an intermediate in the production of various organic compounds. However, it is important to handle this compound with care as it may pose health and environmental hazards if not managed properly.

InChI:InChI=1/C17H11N3O4S/c1-10(21)24-13-7-3-2-6-12(13)15-18-17-20(19-15)16(22)14(25-17)9-11-5-4-8-23-11/h2-9H,1H3/b14-9+

Synthetic route

3-quinuclidinecarboxylic acid ethyl ester (6238-33-1) → quinuclidine-3-carboxylic acid (75208-40-1)

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

3-quinuclidinecarboxylic acid ethyl ester (6238-33-1) → 3-hydroxymethyl-1-azabicyclo[2.2.2]octane (5176-22-7)

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

3-quinuclidinecarboxylic acid ethyl ester (6238-33-1) → 1-azabicyclo<2.2.2>octane-3-carboxylic acid hydrochloride (6238-34-2)

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

thiophene (188290-36-0) + bromobenzene (108-86-1) + 3-quinuclidinecarboxylic acid ethyl ester (6238-33-1) + phenyllithium (591-51-5) → di(2-thienyl)(3-quinuclidyl)carbinol hydrochloride (57734-76-6)

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%

thiophene (188290-36-0) + bromobenzene (108-86-1) + 3-quinuclidinecarboxylic acid ethyl ester (6238-33-1) → di(2-thienyl)(3-quinuclidyl)carbinol hydrochloride (57734-76-6)

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%

N-Hydroxy-2-(2-oxo-pyrrolidin-1-yl)-acetamidine (126145-44-6) + 3-quinuclidinecarboxylic acid ethyl ester (6238-33-1) → 1-((5-(1-azabicyclo[2.2.2]octan-3-yl)-1,2,4-oxadiazol-3-yl)methyl)pyrrolidin-2-one

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

2-bromothiophene (1003-09-4) + 3-quinuclidinecarboxylic acid ethyl ester (6238-33-1) → (3-quinuclidyl)(2-thienyl)ketone (60697-86-1)

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

2-bromothiophene (1003-09-4) + 3-quinuclidinecarboxylic acid ethyl ester (6238-33-1) → (3-Quinuclidyl) di(2-thienyl) carbinol (57734-75-5)

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

3-quinuclidinecarboxylic acid ethyl ester (6238-33-1) + thiophen-2-yl magnesium bromide (5713-61-1) → (3-quinuclidyl)(2-thienyl)ketone (60697-86-1)

Conditions	Yield
In diethyl ether

3-quinuclidinecarboxylic acid ethyl ester (6238-33-1) + thiophen-2-yl magnesium bromide (5713-61-1) → (3-Quinuclidyl) di(2-thienyl) carbinol (57734-75-5)

Conditions	Yield
In diethyl ether

furan (110-00-9) + 3-quinuclidinecarboxylic acid ethyl ester (6238-33-1) → (3-Quinuclidyl) di(2-furyl) carbinol (132668-72-5)

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;

3-quinuclidinecarboxylic acid ethyl ester (6238-33-1) → (1-azabicyclo[2.2.2]octan-3-yl)carbonyl chloride (83598-29-2)

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

3-quinuclidinecarboxylic acid ethyl ester (6238-33-1) → N-methoxy-N-methyl-1-azabicyclo<2.2.2>octane-3-formamide (133366-37-7)

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

3-quinuclidinecarboxylic acid ethyl ester (6238-33-1) → 3-benzo[b]thiophen-2-ylmethyl-1-aza-bicyclo[2.2.2]octane

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

3-quinuclidinecarboxylic acid ethyl ester (6238-33-1) → (1-aza-bicyclo[2.2.2]oct-3-yl)-benzo[b]thiophen-2-yl-methanol

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

3-quinuclidinecarboxylic acid ethyl ester (6238-33-1) → (1-aza-bicyclo[2.2.2]oct-3-yl)-benzo[b]thiophen-2-yl-methanone (392287-48-8)

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

3-quinuclidinecarboxylic acid ethyl ester (6238-33-1) → N-methoxy-1-azabicyclo[2.2.2]octane-3-carboxamide (149156-47-8)

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

3-quinuclidinecarboxylic acid ethyl ester (6238-33-1) → (Z)-N-methoxy-1-azabicyclo[2.2.2]octane-3-carboximidoyl chloride (155613-14-2)

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

3-quinuclidinecarboxylic acid ethyl ester (6238-33-1) → [R,S]-α-(methoxyimino)-α-(1-azabicyclo[2.2.2]oct-3-yl)acetonitrile

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

3-quinuclidinecarboxylic acid ethyl ester (6238-33-1) → (+/-) SKB20206 (151433-82-8)

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

3-quinuclidinecarboxylic acid ethyl ester (6238-33-1) → sabcomeline

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

3-quinuclidinecarboxylic acid ethyl ester (6238-33-1) → (S)-1-Aza-bicyclo[2.2.2]oct-3-yl-[(Z)-methoxyimino]-acetonitrile

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

3-quinuclidinecarboxylic acid ethyl ester (6238-33-1) → (Z)-N-methoxy-1-azabicyclo[2.2.2]octane-3-carboximidoyl fluoride

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

3-quinuclidinecarboxylic acid ethyl ester (6238-33-1) → 1,3-dimethyl-4-amino-5-(quinuclid-3-ylcarboxamin)uracil (134580-20-4)

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

3-quinuclidinecarboxylic acid ethyl ester (6238-33-1) → quinuclidine-3-carboxylic acid chloride hydrochloride (66073-50-5)

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

3-quinuclidinecarboxylic acid ethyl ester (6238-33-1) → 1,3-dimethyl-8-(quinuclid-3-yl)xanthine (134580-19-1)

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

3-quinuclidinecarboxylic acid ethyl ester (6238-33-1) → (1-aza-bicyclo[2.2.2]oct-3-yl)-thiophen-2-yl-methanol (62732-41-6, 102723-02-4)

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

3-quinuclidinecarboxylic acid ethyl ester (6238-33-1) → 3- (60698-05-7)

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

Downstream Products

• 57734-75-5 (3-Quinuclidyl) di(2-thienyl) carbinol 
• 5176-22-7 3-hydroxymethyl-1-azabicyclo[2.2.2]octane 
• 75208-40-1 quinuclidine-3-carboxylic acid 
• 6238-34-2 1-azabicyclo<2.2.2>octane-3-carboxylic acid hydrochloride 
• 60698-05-7 3- 
• 159912-53-5 sabcomeline 
• 151433-82-8 (+/-) SKB20206 
• 159912-53-5 α-(methoxyimino)-α-(1-azabicyclo[2.2.2]oct-3-yl)-acetonitrile 
• 57734-76-6 quiditene