tert-butyl (1S,6S)-2-[(E)-methoxyiminomethyl]-9-azabicyclo[4.2.1]non-2-ene-9-carboxylate

Base Information

• Chemical Name: tert-butyl (1S,6S)-2-[(E)-methoxyiminomethyl]-9-azabicyclo[4.2.1]non-2-ene-9-carboxylate
• CAS No.: 125736-19-8
• Molecular Formula: C₁₅H₂₄N₂O₃
• Molecular Weight: 280.367
• Mol file: 125736-19-8.mol

Synonyms:125736-19-8;9-Azabicyclo(4.2.1)non-2-ene-9-carboxylic acid, 2-((methoxyimino)methyl)-, 1,1-dimethylethyl ester, (1R-(1alpha,2(E),6alpha))-

Chemical Property of tert-butyl (1S,6S)-2-[(E)-methoxyiminomethyl]-9-azabicyclo[4.2.1]non-2-ene-9-carboxylate

Chemical Property:

• Vapor Pressure: 8.81E-06mmHg at 25°C
• Boiling Point: 373.7°Cat760mmHg
• Flash Point: 179.8°C
• Density: 1.14g/cm³
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 280.17869263
• Heavy Atom Count: 20
• Complexity: 423

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1C2CCC=C(C1CC2)C=NOC
• Isomeric SMILES: CC(C)(C)OC(=O)N1[C@H]2CCC=C([C@@H]1CC2)/C=N/OC

Technology Process of tert-butyl (1S,6S)-2-[(E)-methoxyiminomethyl]-9-azabicyclo[4.2.1]non-2-ene-9-carboxylate

There total 8 articles about tert-butyl (1S,6S)-2-[(E)-methoxyiminomethyl]-9-azabicyclo[4.2.1]non-2-ene-9-carboxylate 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:

(1R)-2-acetyl-9-(1-tert-butoxycarbonyl)-9-azobicyclo<4.2.1>-2-nonene (90741-53-0) → (1R,6R)-2-(Methoxyimino-methyl)-9-aza-bicyclo[4.2.1]non-2-ene-9-carboxylic acid tert-butyl ester (125736-19-8)

Guidance literature:

Multi-step reaction with 8 steps

1: 1) KHMDS, 2) Et₃N / 1) THF, -78 deg C, 60 min, 2) -78 deg C, 45 minalp

2: MCPBA / hexane / 0.5 h / Ambient temperature

3: aq. HF / acetonitrile / 0.33 h / Ambient temperature

4: NaIO₄ / H₂O; methanol / 1 h / Ambient temperature

5: oxalyl chloride, DMF / benzene / 1 h / Ambient temperature

6: 1) 4-methylmorpholine / 1) DMF, r.t., 30 min, 2) THF, -10 deg C to r.t.

7: LiAlH₄ / tetrahydrofuran / 0.25 h / -10 °C

8: 1) K₂CO₃, 2) molecular sieves, pyridinium p-toluenesulfonate / 1) THF, H₂O, r.t., 30 min, 2) CH₂Cl₂, r.t., 1h

With 4-methyl-morpholine; sodium periodate; lithium aluminium tetrahydride; molecular sieve; oxalyl dichloride; hydrogen fluoride; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; potassium carbonate; triethylamine; N,N-dimethyl-formamide; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; hexane; water; acetonitrile; benzene;

DOI:10.1021/jo00296a050

Reference yield:

(1R)-9-(tert-butoxycarbonyl)-2-(2-hydroxyacetyl)-9-azabicyclo<4.2.1>non-2-ene (125736-13-2) → (1R,6R)-2-(Methoxyimino-methyl)-9-aza-bicyclo[4.2.1]non-2-ene-9-carboxylic acid tert-butyl ester (125736-19-8)

Guidance literature:

Multi-step reaction with 5 steps

1: NaIO₄ / H₂O; methanol / 1 h / Ambient temperature

2: oxalyl chloride, DMF / benzene / 1 h / Ambient temperature

3: 1) 4-methylmorpholine / 1) DMF, r.t., 30 min, 2) THF, -10 deg C to r.t.

4: LiAlH₄ / tetrahydrofuran / 0.25 h / -10 °C

5: 1) K₂CO₃, 2) molecular sieves, pyridinium p-toluenesulfonate / 1) THF, H₂O, r.t., 30 min, 2) CH₂Cl₂, r.t., 1h

With 4-methyl-morpholine; sodium periodate; lithium aluminium tetrahydride; molecular sieve; oxalyl dichloride; pyridinium p-toluenesulfonate; potassium carbonate; N,N-dimethyl-formamide; In tetrahydrofuran; methanol; water; benzene;

DOI:10.1021/jo00296a050

Reference yield:

(1R)-9-(tert-butoxycarbonyl)-2-<1-(tert-butyldimethylsiloxy)-ethenyl>-9-azabicyclo<4.2.1>non-2-ene (125736-11-0) → (1R,6R)-2-(Methoxyimino-methyl)-9-aza-bicyclo[4.2.1]non-2-ene-9-carboxylic acid tert-butyl ester (125736-19-8)

Guidance literature:

Multi-step reaction with 7 steps

1: MCPBA / hexane / 0.5 h / Ambient temperature

2: aq. HF / acetonitrile / 0.33 h / Ambient temperature

3: NaIO₄ / H₂O; methanol / 1 h / Ambient temperature

4: oxalyl chloride, DMF / benzene / 1 h / Ambient temperature

5: 1) 4-methylmorpholine / 1) DMF, r.t., 30 min, 2) THF, -10 deg C to r.t.

6: LiAlH₄ / tetrahydrofuran / 0.25 h / -10 °C

7: 1) K₂CO₃, 2) molecular sieves, pyridinium p-toluenesulfonate / 1) THF, H₂O, r.t., 30 min, 2) CH₂Cl₂, r.t., 1h

With 4-methyl-morpholine; sodium periodate; lithium aluminium tetrahydride; molecular sieve; oxalyl dichloride; hydrogen fluoride; pyridinium p-toluenesulfonate; potassium carbonate; N,N-dimethyl-formamide; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; hexane; water; acetonitrile; benzene;

DOI:10.1021/jo00296a050

upstream raw materials:

N-methoxylamine hydrochloride

(1R)-9-(tert-butoxycarbonyl)-2-formyl-9-azabicyclo<4.2.1>non-2-ene

(1R)-2-acetyl-9-(1-tert-butoxycarbonyl)-9-azobicyclo<4.2.1>-2-nonene

(1R)-9-(tert-butoxycarbonyl)-2-(chlorocarbonyl)-9-azabicyclo<4.2.1>non-2-ene

Refernces