(3S,5R,8aS)-(+)-Hexahydro-3-phenyl-5H-oxazolo[3,2-a]pyridine-5-carbonitrile

Base Information

• Chemical Name: (3S,5R,8aS)-(+)-Hexahydro-3-phenyl-5H-oxazolo[3,2-a]pyridine-5-carbonitrile
• CAS No.: 106565-71-3
• Molecular Formula: C14H16N2O
• Molecular Weight: 228.29
• Hs Code.: 2934999090
• European Community (EC) Number: 634-598-5
• DSSTox Substance ID: DTXSID60893657
• Nikkaji Number: J1.880.810B
• Wikidata: Q81987731
• Mol file: 106565-71-3.mol

Synonyms:106565-71-3;(3S,5R,8aS)-(+)-Hexahydro-3-phenyl-5H-oxazolo[3,2-a]pyridine-5-carbonitrile;(+)-2-Cyano-6-phenyloxazolopiperidine;(3S,5R,8aS)-3-Phenylhexahydro-2H-oxazolo[3,2-a]pyridine-5-carbonitrile;(3S,5R,8aS)-3-phenyl-3,5,6,7,8,8a-hexahydro-2H-[1,3]oxazolo[3,2-a]pyridine-5-carbonitrile;(3S,5R,8aS)-3-phenylhexahydro-5H-oxazolo[3,2-a]pyridine-5-carbonitrile;EC 634-598-5;AMY729;SCHEMBL16481379;DTXSID60893657;AKOS025396071;(3S,5R,8aS)-3-Phenyl-3,5,6,7,8,8a-hexahydro-2H-oxazolo[3,2-a]pyridine-5-carbonitrile;AC-33545;AS-52494;CS-0054560;P15256;(3s 5r 8As)-(+)-hexahydro-3-phenyl-5H-o&;J-001610;(3S,5R,8aS)-(+)-Hexahydro-3-phenyl-5H-oxazolo[3,2-a]pyridine-5-carbonitrile, 97%;(3S,5R,8aS)-3-phenyl-3,5,6,7,8,8a-hexahydro-2H-oxazolo[2,3-f]pyridine-5-carbonitrile

Chemical Property of (3S,5R,8aS)-(+)-Hexahydro-3-phenyl-5H-oxazolo[3,2-a]pyridine-5-carbonitrile

Chemical Property:

• Vapor Pressure: 2.23E-06mmHg at 25°C
• Melting Point: 79-83 °C(lit.)
• Refractive Index: 1.593
• Boiling Point: 392.817 °C at 760 mmHg
• Flash Point: 191.369 °C
• PSA: 36.26000
• Density: 1.187 g/cm³
• LogP: 2.39998
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 228.126263138
• Heavy Atom Count: 17
• Complexity: 315

Purity/Quality:

99.9% ^*data from raw suppliers

(3S,5R,8aS)-(+)-Hexahydro-3-phenyl-5H-oxazolo[3,2-a]pyridine-5-carbonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(N2C(C1)OCC2C3=CC=CC=C3)C#N
• Isomeric SMILES: C1C[C@@H](N2[C@H](C1)OC[C@@H]2C3=CC=CC=C3)C#N
• Uses: (3S,5R,8aS)-(+)-Hexahydro-3-phenyl-5H-oxazolo[3,2-a]pyridine-5-carbonitrile can be used as a starting material:To prepare spirocyclic aminochroman derivatives as possible 5-HT1A agonists.In the asymmetric synthesis of aza-analogs of podophyllotoxin as potent antitumor agents.

Technology Process of (3S,5R,8aS)-(+)-Hexahydro-3-phenyl-5H-oxazolo[3,2-a]pyridine-5-carbonitrile

There total 1 articles about (3S,5R,8aS)-(+)-Hexahydro-3-phenyl-5H-oxazolo[3,2-a]pyridine-5-carbonitrile 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: 53.0%

potassium cyanide + (2S)-2-phenylglycinol (20989-17-7) + Glutaraldehyde (111-30-8,29257-65-6,79215-57-9) → (3S)-3-phenylhexahydro-2H-oxazolo[3,2-a]pyridine-5-carbonitrile + (3S,5R,8aS)-3-phenylhexahydro-2H-oxazolo[3,2-a]pyridine-5-carbonitrile (106565-71-3)

Guidance literature:

potassium cyanide; (2S)-2-phenylglycinol; Glutaraldehyde; With citric acid; In dichloromethane; water; at 2 - 5 ℃;

With zinc(II) trifluoroacetate; In dichloromethane; at 20 - 25 ℃; optical yield given as %de; Inert atmosphere;

DOI:10.1021/op1002227

Reference yield: 65.0%

(3S,5R,8aS)-3-phenylhexahydro-2H-oxazolo[3,2-a]pyridine-5-carbonitrile (106565-71-3) + 1-Iod-4,4-dimethoxypentan (88794-75-6) → (3S,5S,8aS)-5-(4,4-Dimethoxy-pentyl)-3-phenyl-hexahydro-oxazolo[3,2-a]pyridine-5-carbonitrile (106507-96-4)

Guidance literature:

With lithium diisopropyl amide; at -78 ℃; for 1.5h;

DOI:10.1016/S0040-4039(00)84315-4

Reference yield:

tert-butyl 3-oxoazetidine-1-carboxylate (398489-26-4) + (3S,5R,8aS)-3-phenylhexahydro-2H-oxazolo[3,2-a]pyridine-5-carbonitrile (106565-71-3) → 3-((3S,5R,8aS)-5-cyano-3-phenyl-hexahydro-oxazolo[3,2-a] pyridin-5-yl)-3-hydroxy-azetidine-1-carboxylic acid tert-butyl ester (1597407-55-0)

Guidance literature:

(3S,5R,8aS)-3-phenylhexahydro-2H-oxazolo[3,2-a]pyridine-5-carbonitrile; With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; lithium diisopropyl amide; In tetrahydrofuran; n-heptane; ethylbenzene; at -80 - -70 ℃; for 2.5h;

tert-butyl 3-oxoazetidine-1-carboxylate; In tetrahydrofuran; n-heptane; ethylbenzene; at -80 - -70 ℃; for 1.5h;

upstream raw materials:

(2S)-2-phenylglycinol

Glutaraldehyde

Downstream raw materials:

(3S,5S,8aS)-5-Benzo[1,3]dioxol-5-ylmethyl-3-phenyl-hexahydro-oxazolo[3,2-a]pyridine-5-carbonitrile

(3S,5S,8aS)-5-(4,4-Dimethoxy-pentyl)-3-phenyl-hexahydro-oxazolo[3,2-a]pyridine-5-carbonitrile

(-)-pumiliotoxin C

(S)-8-Methyl-3-phenyl-5-propyl-decahydro-oxazolo[2,3-j]quinoline

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