(-)-alpha-Conhydrine

Base Information

• Chemical Name: (-)-alpha-Conhydrine
• CAS No.: 18209-37-5
• Molecular Formula: C₈H₁₇NO
• Molecular Weight: 143.229
• European Community (EC) Number: 207-798-1
• DSSTox Substance ID: DTXSID101290988
• Nikkaji Number: J83.316I
• Wikipedia: Conhydrine
• Mol file: 18209-37-5.mol

Synonyms:alpha-conhydrine;conhydrine

Chemical Property of (-)-alpha-Conhydrine

Chemical Property:

• XLogP3: 1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 143.131014166
• Heavy Atom Count: 10
• Complexity: 95.3

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCC(C1CCCCN1)O
• Isomeric SMILES: CC[C@@H]([C@H]1CCCCN1)O

Technology Process of (-)-alpha-Conhydrine

There total 35 articles about (-)-alpha-Conhydrine 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: 96.0%

conhydrinone hydrochloride (38726-77-1) → C8H17NO (63401-12-7) + (S)-1-[(R)-piperidin-2-yl]propan-1-ol [(-)-α-conhydrine] (495-20-5,3238-62-8,3238-63-9,18209-37-5,63401-12-7,100101-26-6)

Guidance literature:

With RuCl₂[(S)-XylSDP][(R,R)-DPEN]; potassium tert-butylate; hydrogen; In isopropyl alcohol; at 20 ℃; under 38002.6 Torr; optical yield given as %ee; enantioselective reaction; Autoclave;

DOI:10.1021/ol901605a

Reference yield: 86.0%

(R)-6-[(S)-1-(benzyloxy)propyl]-1,2,3,6-tetrahydropyridine (1403599-36-9) → (S)-1-[(R)-piperidin-2-yl]propan-1-ol [(-)-α-conhydrine] (495-20-5,3238-62-8,3238-63-9,18209-37-5,63401-12-7,100101-26-6)

Guidance literature:

With hydrogenchloride; palladium 10% on activated carbon; hydrogen; In ethanol; for 24h; under 3102.97 Torr; Inert atmosphere;

DOI:10.1002/ejoc.201200489

Reference yield: 74.0%

(R)-6-((S)-1-(tert-butyldimethylsilyloxy)propyl)piperidin-2-one (1210445-07-0) → (S)-1-[(R)-piperidin-2-yl]propan-1-ol [(-)-α-conhydrine] (495-20-5,3238-62-8,3238-63-9,18209-37-5,63401-12-7,100101-26-6)

Guidance literature:

(R)-6-((S)-1-(tert-butyldimethylsilyloxy)propyl)piperidin-2-one; With lithium aluminium tetrahydride; In tetrahydrofuran; tert-butyl methyl ether; at 0 ℃; for 2h; Inert atmosphere;

In tetrahydrofuran; tert-butyl methyl ether; at 20 ℃; for 1h; Inert atmosphere;

DOI:10.1016/j.tetlet.2009.12.039

upstream raw materials:

2-(1-hydroxypropyl)-piperidine-1-carboxylic acid tert-butyl ester

(+)-(5R,6S,S_S)-methyl 5-(tert-butylsulfinamido)-6-(methoxymethoxy)-8-(trimethylsilyl)oct-7-ynoate

(+)-(6R)-[(1S)-1-(methoxymethoxy)-3-(trimethylsilyl)prop-2-ynyl]piperidin-2-one

(+)-(6R)-[(1S)-1-(methoxymethoxy)prop-2-ynyl]piperidin-2-one

Refernces

• 1、 Bandini, Elisa,Corda, Giulia,D'Aurizio, Antonio,Panunzio, Mauro. "A straightforward synthesis of conhydrine by hetero Diels-Alder strategy mediated by microwaves". supporting information; experimental part. p. 933 - 934. Retrieved 2010/05/18.
• 2、 Voituriez, Arnaud,Ferreira, Franck,Chemla, Fabrice. "Short and efficient asymmetric synthesis of (-)-α-conhydrine". . p. 5358 - 5361. Retrieved 2008/02/08.