Benzoic acid (1S,2S,3R,5R)-2-carbamoyl-8-aza-bicyclo[3.2.1]oct-3-yl ester

Base Information

• Chemical Name: Benzoic acid (1S,2S,3R,5R)-2-carbamoyl-8-aza-bicyclo[3.2.1]oct-3-yl ester
• CAS No.: 208038-11-3
• Molecular Formula: C₁₅H₁₈N₂O₃
• Molecular Weight: 274.32
• Mol file: 208038-11-3.mol

Synonyms:

Chemical Property of Benzoic acid (1S,2S,3R,5R)-2-carbamoyl-8-aza-bicyclo[3.2.1]oct-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid (1S,2S,3R,5R)-2-carbamoyl-8-aza-bicyclo[3.2.1]oct-3-yl ester

There total 14 articles about Benzoic acid (1S,2S,3R,5R)-2-carbamoyl-8-aza-bicyclo[3.2.1]oct-3-yl ester 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:

(1S,5R)-8-benzyl-8-azabicyclo[3.2.1]octan-2-one (208038-01-1) → Benzoic acid (1S,2S,3R,5R)-2-carbamoyl-8-aza-bicyclo[3.2.1]oct-3-yl ester (208038-11-3)

Guidance literature:

Multi-step reaction with 9 steps

1: H₂ / Pd/C / methanol / 5 h

2: methanol / 2 h / Ambient temperature

3: NaH / toluene / 1.) room temperature, 30 min, 2.) reflux, 5 h

4: Na₂CO₃*H₂O / tetrahydrofuran; H₂O / 16 h

5: aq. NaOH / ethanol / 1.) 0 deg C, 1 h, 2.) room temperature, 1.5 h

6: 0.67 h / 105 - 110 °C

7: Na₂CO₃, aq. H₂O₂ / H₂O / 24 h / Ambient temperature

8: DMAP / CH₂Cl₂ / 12 h / Ambient temperature

9: TFA / CH₂Cl₂ / 1 h / Ambient temperature

With dmap; sodium hydroxide; hydrogen; dihydrogen peroxide; sodium hydride; sodium carbonate; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; toluene;

DOI:10.1021/jo980153t

Reference yield:

(2S,5R)-5-(2-Carboxy-ethyl)-pyrrolidine-2-carboxylic acid tert-butyl ester → Benzoic acid (1S,2S,3R,5R)-2-carbamoyl-8-aza-bicyclo[3.2.1]oct-3-yl ester (208038-11-3)

Guidance literature:

Multi-step reaction with 13 steps

1: AcCl / 14 h / Heating

2: K₂CO₃ / acetonitrile / 14 h / Ambient temperature

3: KHMDS / tetrahydrofuran / 1 h / -78 °C

4: NaI / pyridine / 8 h / Heating

5: H₂ / Pd/C / methanol / 5 h

6: methanol / 2 h / Ambient temperature

7: NaH / toluene / 1.) room temperature, 30 min, 2.) reflux, 5 h

8: Na₂CO₃*H₂O / tetrahydrofuran; H₂O / 16 h

9: aq. NaOH / ethanol / 1.) 0 deg C, 1 h, 2.) room temperature, 1.5 h

10: 0.67 h / 105 - 110 °C

11: Na₂CO₃, aq. H₂O₂ / H₂O / 24 h / Ambient temperature

12: DMAP / CH₂Cl₂ / 12 h / Ambient temperature

13: TFA / CH₂Cl₂ / 1 h / Ambient temperature

With dmap; sodium hydroxide; hydrogen; dihydrogen peroxide; potassium hexamethylsilazane; sodium hydride; sodium carbonate; potassium carbonate; acetyl chloride; trifluoroacetic acid; sodium iodide; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; ethanol; dichloromethane; water; toluene; acetonitrile;

DOI:10.1021/jo980153t

Reference yield:

(2S,5R)-5-[1'-(2'-methoxycarbonyl)ethyl]proline methyl ester → Benzoic acid (1S,2S,3R,5R)-2-carbamoyl-8-aza-bicyclo[3.2.1]oct-3-yl ester (208038-11-3)

Guidance literature:

Multi-step reaction with 12 steps

1: K₂CO₃ / acetonitrile / 14 h / Ambient temperature

2: KHMDS / tetrahydrofuran / 1 h / -78 °C

3: NaI / pyridine / 8 h / Heating

4: H₂ / Pd/C / methanol / 5 h

5: methanol / 2 h / Ambient temperature

6: NaH / toluene / 1.) room temperature, 30 min, 2.) reflux, 5 h

7: Na₂CO₃*H₂O / tetrahydrofuran; H₂O / 16 h

8: aq. NaOH / ethanol / 1.) 0 deg C, 1 h, 2.) room temperature, 1.5 h

9: 0.67 h / 105 - 110 °C

10: Na₂CO₃, aq. H₂O₂ / H₂O / 24 h / Ambient temperature

11: DMAP / CH₂Cl₂ / 12 h / Ambient temperature

12: TFA / CH₂Cl₂ / 1 h / Ambient temperature

With dmap; sodium hydroxide; hydrogen; dihydrogen peroxide; potassium hexamethylsilazane; sodium hydride; sodium carbonate; potassium carbonate; trifluoroacetic acid; sodium iodide; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; ethanol; dichloromethane; water; toluene; acetonitrile;

DOI:10.1021/jo980153t

upstream raw materials:

(1S,2S,3R,5R)-3-Benzoyloxy-2-carbamoyl-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester

(1S,5R)-8-benzyl-8-azabicyclo[3.2.1]octan-2-one

tert-butyl (1S,5R)-8-azabicyclo[3.2.1]oct-2-ene-8-carboxylate

(1S,5R)-8-(tert-butyloxycarbonyl)-8-azabicyclo[3.2.1]-2-octanone

Downstream raw materials:

(+)-cocaine

benzoylecgonine

Benzoic acid (1S,2S,3R,5R)-2-carbamoyl-8-methyl-8-aza-bicyclo[3.2.1]oct-3-yl ester