(1R,3R,5S)-3-Benzyloxy-8-(toluene-4-sulfonyl)-8-aza-bicyclo[3.2.1]octane

Base Information

• Chemical Name: (1R,3R,5S)-3-Benzyloxy-8-(toluene-4-sulfonyl)-8-aza-bicyclo[3.2.1]octane
• CAS No.: 115522-42-4
• Molecular Formula: C₂₁H₂₅NO₃S
• Molecular Weight: 371.5
• Mol file: 115522-42-4.mol

Synonyms:(1R,3R,5S)-3-Benzyloxy-8-(toluene-4-sulfonyl)-8-aza-bicyclo[3.2.1]octane

Chemical Property of (1R,3R,5S)-3-Benzyloxy-8-(toluene-4-sulfonyl)-8-aza-bicyclo[3.2.1]octane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (1R,3R,5S)-3-Benzyloxy-8-(toluene-4-sulfonyl)-8-aza-bicyclo[3.2.1]octane

There total 6 articles about (1R,3R,5S)-3-Benzyloxy-8-(toluene-4-sulfonyl)-8-aza-bicyclo[3.2.1]octane 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: 90.0%

N-((1R,3S,5R)-3-Benzyloxy-5-chloro-cycloheptyl)-4-methyl-benzenesulfonamide (115522-53-7) → (1R,3R,5S)-3-Benzyloxy-8-(toluene-4-sulfonyl)-8-aza-bicyclo[3.2.1]octane (115522-42-4)

Guidance literature:

With potassium carbonate; In methanol; at 20 ℃; for 1h;

DOI:10.1016/S0040-4039(00)95578-3

Reference yield:

6-(benzyloxy)-1,3-cycloheptadiene (115522-58-2) → (1R,3R,5S)-3-Benzyloxy-8-(toluene-4-sulfonyl)-8-aza-bicyclo[3.2.1]octane (115522-42-4)

Guidance literature:

Multi-step reaction with 6 steps

1: 77 percent / LiCl, p-benzoquinone / Pd(OAc)2 (7percent) / acetic acid

2: 64 percent / Pd(PPh₃)4 (3percent) / acetonitrile; dimethylsulfoxide / 12 h / 20 °C

3: 95 percent / H₂ / RhCl(PPh₃)3 / ethanol / 15 h / 20 °C / 4560 Torr

4: 95 percent / NaOH / methanol; H₂O

5: 95 percent / EtO₂C-N=N-CO₂Et, ZnCl₂, PBu₃ / 3 h / 20 °C

6: 90 percent / K₂CO₃ / methanol / 1 h / 20 °C

With sodium hydroxide; tributylphosphine; hydrogen; potassium carbonate; p-benzoquinone; lithium chloride; zinc(II) chloride; diethylazodicarboxylate; palladium diacetate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; RhCl(PPh₃)3; In methanol; ethanol; water; acetic acid; dimethyl sulfoxide; acetonitrile;

DOI:10.1016/S0040-4039(00)95578-3

Reference yield:

1β-acetoxy-4β-chloro-6α-(benzyloxy)-2-cycloheptene (115522-57-1,150338-86-6) → (1R,3R,5S)-3-Benzyloxy-8-(toluene-4-sulfonyl)-8-aza-bicyclo[3.2.1]octane (115522-42-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 64 percent / Pd(PPh₃)4 (3percent) / acetonitrile; dimethylsulfoxide / 12 h / 20 °C

2: 95 percent / H₂ / RhCl(PPh₃)3 / ethanol / 15 h / 20 °C / 4560 Torr

3: 95 percent / NaOH / methanol; H₂O

4: 95 percent / EtO₂C-N=N-CO₂Et, ZnCl₂, PBu₃ / 3 h / 20 °C

5: 90 percent / K₂CO₃ / methanol / 1 h / 20 °C

With sodium hydroxide; tributylphosphine; hydrogen; potassium carbonate; zinc(II) chloride; diethylazodicarboxylate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; RhCl(PPh₃)3; In methanol; ethanol; water; dimethyl sulfoxide; acetonitrile;

DOI:10.1016/S0040-4039(00)95578-3

upstream raw materials:

N-((1R,3S,5R)-3-Benzyloxy-5-chloro-cycloheptyl)-4-methyl-benzenesulfonamide

6-(benzyloxy)-1,3-cycloheptadiene

1β-acetoxy-4β-chloro-6α-(benzyloxy)-2-cycloheptene

N-((1R,3S,5S)-3-Benzyloxy-5-hydroxy-cycloheptyl)-4-methyl-benzenesulfonamide

Downstream raw materials:

nortropine

3-tropanol

Refernces