(2S,3R)-1-allyl-2-(hydroxymethyl)-3-(para-bromophenyl)-6-(ortho-nosyl)-1,6-diazaspiro[3.3]heptane

Base Information

• Chemical Name: (2S,3R)-1-allyl-2-(hydroxymethyl)-3-(para-bromophenyl)-6-(ortho-nosyl)-1,6-diazaspiro[3.3]heptane
• CAS No.: 1393810-50-8
• Molecular Formula: C₂₁H₂₂BrN₃O₅S
• Molecular Weight: 508.393

Synonyms:

Chemical Property of (2S,3R)-1-allyl-2-(hydroxymethyl)-3-(para-bromophenyl)-6-(ortho-nosyl)-1,6-diazaspiro[3.3]heptane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R)-1-allyl-2-(hydroxymethyl)-3-(para-bromophenyl)-6-(ortho-nosyl)-1,6-diazaspiro[3.3]heptane

There total 9 articles about (2S,3R)-1-allyl-2-(hydroxymethyl)-3-(para-bromophenyl)-6-(ortho-nosyl)-1,6-diazaspiro[3.3]heptane 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:

2-(allyl((1S,2R)-1-(4-bromophenyl)-1,3-dihydroxypropan-2-yl)amino)acetonitrile (1393809-78-3) → (2S,3R)-1-allyl-2-(hydroxymethyl)-3-(para-bromophenyl)-6-(ortho-nosyl)-1,6-diazaspiro[3.3]heptane (1393810-50-8)

Guidance literature:

Multi-step reaction with 12 steps

1.1: triethylamine / dichloromethane / 0 - 20 °C

2.1: pyridine; thionyl chloride / dichloromethane / 0.42 h / 0 °C / Inert atmosphere

3.1: potassium hexamethylsilazane / tetrahydrofuran / 1.25 h / -78 °C

4.1: 1,3-dimethylbarbituric acid; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / dichloromethane; ethanol / 72 h / 40 °C / Inert atmosphere

5.1: dichloromethane / 0 - 20 °C / Inert atmosphere

6.1: tetrahydrofuran / 2 h / -78 °C / Alkaline conditions; Inert atmosphere

6.2: -78 °C / Inert atmosphere

7.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.67 h / -78 °C / Inert atmosphere

7.2: -78 - 20 °C / Inert atmosphere

8.1: diisobutylaluminium hydride / -78 °C / Inert atmosphere

9.1: triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere

10.1: potassium carbonate / acetonitrile / 3 h / 60 °C / Inert atmosphere

11.1: trifluoroacetic acid / dichloromethane / 0 - 20 °C / Inert atmosphere

12.1: potassium carbonate / 3 h / 80 °C / Sealed tube; Inert atmosphere

With pyridine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; thionyl chloride; 1,3-dimethylbarbituric acid; potassium hexamethylsilazane; diisobutylaluminium hydride; potassium carbonate; triethylamine; trifluoroacetic acid; lithium hexamethyldisilazane; In tetrahydrofuran; ethanol; dichloromethane; acetonitrile;

DOI:10.1021/jo300974j

Reference yield:

2-(allyl((1S,2R)-1-(4-bromophenyl)-1-hydroxy-3-(trityloxy)propan-2-yl)amino)acetonitrile (1393809-81-8) → (2S,3R)-1-allyl-2-(hydroxymethyl)-3-(para-bromophenyl)-6-(ortho-nosyl)-1,6-diazaspiro[3.3]heptane (1393810-50-8)

Guidance literature:

Multi-step reaction with 11 steps

1.1: pyridine; thionyl chloride / dichloromethane / 0.42 h / 0 °C / Inert atmosphere

2.1: potassium hexamethylsilazane / tetrahydrofuran / 1.25 h / -78 °C

3.1: 1,3-dimethylbarbituric acid; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / dichloromethane; ethanol / 72 h / 40 °C / Inert atmosphere

4.1: dichloromethane / 0 - 20 °C / Inert atmosphere

5.1: tetrahydrofuran / 2 h / -78 °C / Alkaline conditions; Inert atmosphere

5.2: -78 °C / Inert atmosphere

6.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.67 h / -78 °C / Inert atmosphere

6.2: -78 - 20 °C / Inert atmosphere

7.1: diisobutylaluminium hydride / -78 °C / Inert atmosphere

8.1: triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere

9.1: potassium carbonate / acetonitrile / 3 h / 60 °C / Inert atmosphere

10.1: trifluoroacetic acid / dichloromethane / 0 - 20 °C / Inert atmosphere

11.1: potassium carbonate / 3 h / 80 °C / Sealed tube; Inert atmosphere

With pyridine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; thionyl chloride; 1,3-dimethylbarbituric acid; potassium hexamethylsilazane; diisobutylaluminium hydride; potassium carbonate; triethylamine; trifluoroacetic acid; lithium hexamethyldisilazane; In tetrahydrofuran; ethanol; dichloromethane; acetonitrile;

DOI:10.1021/jo300974j

Reference yield:

2-(allyl((1S,2R)-1-(4-bromophenyl)-1-chloro-3-(trityloxy)propan-2-yl)amino)acetonitrile (1393809-83-0) → (2S,3R)-1-allyl-2-(hydroxymethyl)-3-(para-bromophenyl)-6-(ortho-nosyl)-1,6-diazaspiro[3.3]heptane (1393810-50-8)

Guidance literature:

Multi-step reaction with 10 steps

1.1: lithium hexamethyldisilazane / tetrahydrofuran / 1.25 h / -50 °C / Inert atmosphere

2.1: 1,3-dimethylbarbituric acid; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / dichloromethane; ethanol / 72 h / 40 °C / Inert atmosphere

3.1: dichloromethane / 0 - 20 °C / Inert atmosphere

4.1: tetrahydrofuran / 2 h / -78 °C / Alkaline conditions; Inert atmosphere

4.2: -78 °C / Inert atmosphere

5.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.67 h / -78 °C / Inert atmosphere

5.2: -78 - 20 °C / Inert atmosphere

6.1: diisobutylaluminium hydride / -78 °C / Inert atmosphere

7.1: triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere

8.1: potassium carbonate / acetonitrile / 3 h / 60 °C / Inert atmosphere

9.1: trifluoroacetic acid / dichloromethane / 0 - 20 °C / Inert atmosphere

10.1: potassium carbonate / 3 h / 80 °C / Sealed tube; Inert atmosphere

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; 1,3-dimethylbarbituric acid; diisobutylaluminium hydride; potassium carbonate; triethylamine; trifluoroacetic acid; lithium hexamethyldisilazane; In tetrahydrofuran; ethanol; dichloromethane; acetonitrile;

DOI:10.1021/jo300974j

upstream raw materials:

(2S,3S,4R)-1-[(tert-butyloxy)carbonyl]-2-(trityloxymethyl)-3-(para-bromophenyl)-4-cyanoazetidine

2-(allyl((1S,2R)-1-(4-bromophenyl)-1,3-dihydroxypropan-2-yl)amino)acetonitrile

2-(allyl((1S,2R)-1-(4-bromophenyl)-1-hydroxy-3-(trityloxy)propan-2-yl)amino)acetonitrile

allyl bromide

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