(5-Ethenyl-1-azabicyclo[2.2.2]octan-2-yl)methanol

Base Information

• Chemical Name: (5-Ethenyl-1-azabicyclo[2.2.2]octan-2-yl)methanol
• CAS No.: 207129-36-0
• Molecular Formula: C10H17NO
• Molecular Weight: 167.25
• European Community (EC) Number: 606-607-2,606-608-8
• Mol file: 207129-36-0.mol

Synonyms:Quincoridine;(5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl)methanol;207129-35-9;207129-36-0;MFCD08276491;(1S,2S,5S)-2-(Hydroxymethyl)-5-vinylquinuclidine;((1S,2R,5R)-5-Vinylquinuclidin-2-yl)methanol;((1S,2S,5S)-5-Vinylquinuclidin-2-yl)methanol;[(1S,2S,5S)-5-Vinylquinuclidin-2-yl]methanol;SCHEMBL20985119;MFCD08275406;SB44907;SB45195;SY235187;Q0074;Q0076;(1S,2R,5R)-5-Vinyl-2-quinuclidinemethanol;(1S,2S,5S)-5-Vinyl-2-quinuclidinemethanol;A879479;A879480;(1S,2R,5R)-2-(Hydroxymethyl)-5-vinylquinuclidine

Chemical Property of (5-Ethenyl-1-azabicyclo[2.2.2]octan-2-yl)methanol

Chemical Property:

• Refractive Index: n20/D 1.515
• Boiling Point: 267 °C(lit.)
• Flash Point: >230 °F
• PSA: 23.47000
• Density: 1.073 g/mL at 25 °C(lit.)
• LogP: 0.81300
• Storage Temp.: 2-8°C
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 167.131014166
• Heavy Atom Count: 12
• Complexity: 181

Purity/Quality:

98%,99%, ^*data from raw suppliers

Quincoridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-36-22
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C=CC1CN2CCC1CC2CO
• Uses: Valuable building block for medicinal chemistry. The skeleton of this compound is identical to the framework of cinchona alkaloids. Possible applications include resolving agents, chiral stationary phases, and chiral ligands in asymmetric synthesis.

Technology Process of (5-Ethenyl-1-azabicyclo[2.2.2]octan-2-yl)methanol

There total 28 articles about (5-Ethenyl-1-azabicyclo[2.2.2]octan-2-yl)methanol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 78.0%

O-(tert-butyldimethylsilyl)quincorine → [(2S,4S,5R)-2-hydroxymethyl-5-vinyl-2-quinuclidine] (207129-36-0)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1039/c1ob05219e

Reference yield:

((1R,2R,4R,5R)-4,5-bis(benzyloxy)-2-(iodomethyl)cyclohexyl)methanol (956006-07-8) → [(2S,4S,5R)-2-hydroxymethyl-5-vinyl-2-quinuclidine] (207129-36-0)

Guidance literature:

Multi-step reaction with 14 steps

1.1: indium(III) chloride / dichloromethane / 0.67 h / 20 °C / Inert atmosphere

1.2: Inert atmosphere; UV-irradiation

2.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere

2.2: -78 - 20 °C / Inert atmosphere

3.1: samarium diiodide / tetrahydrofuran; methanol / Inert atmosphere

4.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

5.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 48 h

6.1: / dichloromethane / Inert atmosphere

7.1: sodium tetrahydroborate / methanol / 1 h / 0 °C / Inert atmosphere

8.1: lipase acrylic resin (Candida antarctica) / dichloromethane / 168 h / Inert atmosphere

9.1: tributylphosphine / tetrahydrofuran / 60 °C / Inert atmosphere

10.1: dihydrogen peroxide / tetrahydrofuran; water / 12 h / Inert atmosphere

11.1: sodium methylate / methanol / 5 h / Inert atmosphere

12.1: 1H-imidazole; iodine; triphenylphosphine / tetrahydrofuran / 1.25 h / 0 °C / Inert atmosphere

13.1: ammonia / methanol / 12 h / Inert atmosphere

14.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

With 1H-imidazole; indium(III) chloride; sodium tetrahydroborate; n-butyllithium; samarium diiodide; tributylphosphine; di-isopropyl azodicarboxylate; palladium 10% on activated carbon; tetrabutyl ammonium fluoride; ammonia; hydrogen; dihydrogen peroxide; iodine; sodium methylate; triphenylphosphine; In tetrahydrofuran; methanol; hexane; dichloromethane; water; ethyl acetate; 4.1: Mitsunobu reaction;

DOI:10.1039/c1ob05219e

Reference yield:

(S)-3-((S)-1-((1R,2R,4R,5R)-4,5-bis(benzyloxy)-2-(hydroxymethyl)cyclohexyl)-3-(tert-butyldimethylsilyloxy)propan-2-ylamino)-4-benzyloxazolidin-2-one (956006-11-4) → [(2S,4S,5R)-2-hydroxymethyl-5-vinyl-2-quinuclidine] (207129-36-0)

Guidance literature:

Multi-step reaction with 13 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere

1.2: -78 - 20 °C / Inert atmosphere

2.1: samarium diiodide / tetrahydrofuran; methanol / Inert atmosphere

3.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

4.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 48 h

5.1: / dichloromethane / Inert atmosphere

6.1: sodium tetrahydroborate / methanol / 1 h / 0 °C / Inert atmosphere

7.1: lipase acrylic resin (Candida antarctica) / dichloromethane / 168 h / Inert atmosphere

8.1: tributylphosphine / tetrahydrofuran / 60 °C / Inert atmosphere

9.1: dihydrogen peroxide / tetrahydrofuran; water / 12 h / Inert atmosphere

10.1: sodium methylate / methanol / 5 h / Inert atmosphere

11.1: 1H-imidazole; iodine; triphenylphosphine / tetrahydrofuran / 1.25 h / 0 °C / Inert atmosphere

12.1: ammonia / methanol / 12 h / Inert atmosphere

13.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

With 1H-imidazole; sodium tetrahydroborate; n-butyllithium; samarium diiodide; tributylphosphine; di-isopropyl azodicarboxylate; palladium 10% on activated carbon; tetrabutyl ammonium fluoride; ammonia; hydrogen; dihydrogen peroxide; iodine; sodium methylate; triphenylphosphine; In tetrahydrofuran; methanol; hexane; dichloromethane; water; ethyl acetate; 3.1: Mitsunobu reaction;

DOI:10.1039/c1ob05219e

upstream raw materials:

((1R,2R,4R,5R)-4,5-bis(benzyloxy)-2-(iodomethyl)cyclohexyl)methanol

(S)-3-((S)-1-((1R,2R,4R,5R)-4,5-bis(benzyloxy)-2-(hydroxymethyl)cyclohexyl)-3-(tert-butyldimethylsilyloxy)propan-2-ylamino)-4-benzyloxazolidin-2-one

N-((S)-1-((1R,2R,4R,5R)-4,5-bis(benzyloxy)-2-(hydroxymethyl)cyclohexyl)-3-(tert-butyldimethylsilyloxy)propan-2-yl)-2,2,2-trifluoroacetamide

1-((3S,4aR,6R,7R,8aR)-6,7-bis(benzyloxy)-3-((tert-butyldimethylsilyloxy)methyl)octahydroisoquinolin-2-(1H)-yl)-2,2,2-trifluoroethanone

Downstream raw materials:

10,11-didehydroquincorine

((2S,4S,5R)-5-Ethyl-1-aza-bicyclo[2.2.2]oct-2-yl)-methanol

Refernces

• 1、 Friestad, Gregory K.,Ji, An,Korapala, Chandra Sekhar,Qin, Jun. "Intermolecular radical addition to N-acylhydrazones as a stereocontrol strategy for alkaloid synthesis: Formal synthesis of quinine". . p. 4039 - 4043. Retrieved 2011/06/28.