(1R,4S)-2-(p-Methoxybenzyl)-2-azabicylo<2.2.1>heptane-3,6-dione

Base Information

• Chemical Name: (1R,4S)-2-(p-Methoxybenzyl)-2-azabicylo<2.2.1>heptane-3,6-dione
• CAS No.: 168773-57-7
• Molecular Formula: C₁₄H₁₅NO₃
• Molecular Weight: 245.278
• Mol file: 168773-57-7.mol

Synonyms:(1R,4S)-2-(p-Methoxybenzyl)-2-azabicylo<2.2.1>heptane-3,6-dione

Chemical Property of (1R,4S)-2-(p-Methoxybenzyl)-2-azabicylo<2.2.1>heptane-3,6-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,4S)-2-(p-Methoxybenzyl)-2-azabicylo<2.2.1>heptane-3,6-dione

There total 15 articles about (1R,4S)-2-(p-Methoxybenzyl)-2-azabicylo<2.2.1>heptane-3,6-dione 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: 97.0%

(1R,4S,6S)-6-Hydroxy-2-(p-methoxybenzyl)-2-azabicyclo<2.2.1>-3-heptanone (168773-55-5) → (1R,4S)-2-(p-Methoxybenzyl)-2-azabicylo<2.2.1>heptane-3,6-dione (168773-57-7)

Guidance literature:

(1R,4S,6S)-6-Hydroxy-2-(p-methoxybenzyl)-2-azabicyclo<2.2.1>-3-heptanone; With oxalyl dichloride; dimethyl sulfoxide; In dichloromethane; at -78 ℃; for 0.166667h; Inert atmosphere;

With triethylamine; In dichloromethane; at -78 - 20 ℃;

DOI:10.1021/jo100710h

Reference yield:

p-Methoxybenzyl bromide (2746-25-0) → (1R,4S)-2-(p-Methoxybenzyl)-2-azabicylo<2.2.1>heptane-3,6-dione (168773-57-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 90 percent / NaH, TBAI / tetrahydrofuran / 1.) 15 min, 2.) 21 h

2: 97 percent / TBAF / tetrahydrofuran / 0.33 h

3: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 1 h, 2.) -78 deg C to r.t., 20 min; r.t., 40 min

With oxalyl dichloride; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran;

DOI:10.1021/jo00119a044

Reference yield:

(5S,6R)-5-Hydroxy-6-<(benzyloxy)methyl>-2-piperidinone (168773-36-2) → (1R,4S)-2-(p-Methoxybenzyl)-2-azabicylo<2.2.1>heptane-3,6-dione (168773-57-7)

Guidance literature:

Multi-step reaction with 9 steps

1: 92 percent / imidazole / dimethylformamide / 15 h

2: 99 percent / NaH, TBAI / tetrahydrofuran / 1.) 15 min, 2.) 42 h

3: 100 percent / H₂ / 10percent Pd/C / ethanol / 23 h

4: 93 percent / CBr₄, PPh₃ / CH₂Cl₂ / 1.) 0 deg C to r.t., 1 h, 2.) r.t., 13 h

5: 99 percent / KHMDS / tetrahydrofuran / 1.) -50 to -35 deg C, 15 min, 2.) -35 deg C, 40 min

6: 99 percent / NH₃, Na, t-BuOH / tetrahydrofuran / 1.) -78 deg C, 6 min, 2.) -78 to -33 deg C, 2 min

7: 90 percent / NaH, TBAI / tetrahydrofuran / 1.) 15 min, 2.) 21 h

8: 97 percent / TBAF / tetrahydrofuran / 0.33 h

9: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 1 h, 2.) -78 deg C to r.t., 20 min; r.t., 40 min

With 1H-imidazole; oxalyl dichloride; carbon tetrabromide; tetrabutyl ammonium fluoride; ammonia; hydrogen; sodium; tetra-(n-butyl)ammonium iodide; potassium hexamethylsilazane; sodium hydride; dimethyl sulfoxide; triethylamine; triphenylphosphine; tert-butyl alcohol; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo00119a044

upstream raw materials:

(1R,4S,6S)-6-Hydroxy-2-(p-methoxybenzyl)-2-azabicyclo<2.2.1>-3-heptanone

p-Methoxybenzyl bromide

(1R,4S,6S)-6-(tert-Butyldimethylsiloxy)-2-benzyl-2-azabicyclo<2.2.1>-3-heptanone

(5S,6R)-1-Benzyl-5-<(tert-butyldimethylsilyl)oxy>-6-(bromomethyl)-2-piperidinone

Downstream raw materials:

Trifluoro-methanesulfonic acid (1R,4S)-2-(4-methoxy-benzyl)-3-oxo-2-aza-bicyclo[2.2.1]hept-5-en-6-yl ester

(1R,4S)-2-(p-Methoxybenzyl)-2-azabicyclo<2.2.1>-5-hepten-3-one

tert-butyl (1R,4S)-(-)-3-oxo-2-azabicyclo[2.2.1]hept-5-ene-2-carboxylate

(1R,4S)-N-(tert-Butyloxycarbonyl)-1-amino-4-(hydroxymethyl)-2-cyclopentene