2-Oxa-5-azabicyclo[2.2.2]octane hemioxalate

Base Information

• Chemical Name: 2-Oxa-5-azabicyclo[2.2.2]octane hemioxalate
• CAS No.: 1523606-41-8
• Molecular Formula: C₂H₂O₄*C₆H₁₁NO
• Molecular Weight: 203.195
• Mol file: 1523606-41-8.mol

Synonyms:2-Oxa-5-azabicyclo[2.2.2]octane oxalate(2:1)

Chemical Property of 2-Oxa-5-azabicyclo[2.2.2]octane hemioxalate

Chemical Property:

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-Oxa-5-azabicyclo[2.2.2]octane hemioxalate

There total 20 articles about 2-Oxa-5-azabicyclo[2.2.2]octane hemioxalate 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:

(2S,5R)-5-hydroxypiperidine-2-carboxylic acid (63088-78-8,448964-01-0,478409-64-2) → (1R,4R)-2-oxa-5-azabicyclo[2.2.2]octane oxalate (1523606-41-8)

Guidance literature:

Multi-step reaction with 8 steps

1.1: sodium hydroxide / water / 1 h / 20 °C / Inert atmosphere

1.2: 10 - 20 °C / Inert atmosphere

2.1: dmap / 12 h / 20 °C / Inert atmosphere

3.1: triethylamine / acetonitrile / 0 - 20 °C / Inert atmosphere

4.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / methanol; toluene / 52 h / 20 °C / Inert atmosphere

5.1: lithium borohydride / ethanol

6.1: 1-methyl-pyrrolidin-2-one / N,N-dimethyl-formamide / 72 h / 100 °C

7.1: 1-dodecylthiol; sodium hydroxide / methanol; acetonitrile / 1.5 h / 50 °C / Inert atmosphere

8.1: acetonitrile / 20 - 50 °C / Inert atmosphere

With 1-methyl-pyrrolidin-2-one; dmap; lithium borohydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; sodium hydroxide; 1-dodecylthiol; In methanol; ethanol; water; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1021/acs.oprd.1c00098

Reference yield:

(2S,5R)-5-hydroxypiperidine-2-carboxylic acid (63088-78-8,448964-01-0,478409-64-2) → (1S,4S)-2-oxa-5-azabicyclo[2.2.2]octane oxalate (1523606-41-8)

Guidance literature:

Multi-step reaction with 6 steps

1.1: sodium hydroxide / water / 1 h / 20 °C / Inert atmosphere

1.2: 10 - 20 °C / Inert atmosphere

2.1: calcium chloride / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere

2.2: 1 h / 0 °C / Inert atmosphere

3.1: dmap; 4-methyl-morpholine / dichloromethane / 0 - 20 °C / Inert atmosphere

4.1: potassium carbonate / N,N-dimethyl-formamide / 80 °C / Inert atmosphere

5.1: potassium carbonate; mercaptoacetic acid / methanol / 50 °C / Inert atmosphere

6.1: acetonitrile / 20 - 50 °C / Inert atmosphere

With 4-methyl-morpholine; dmap; potassium carbonate; mercaptoacetic acid; calcium chloride; sodium hydroxide; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/acs.oprd.1c00098

Reference yield:

(1S,4S)-5-(4-nitrophenylsulfonyl)-2-oxa-5-aza-bicyclo [2.2.2]octan-3-one → (1R,4R)-2-oxa-5-azabicyclo[2.2.2]octane oxalate (1523606-41-8)

Guidance literature:

Multi-step reaction with 7 steps

1: dmap / 12 h / 20 °C / Inert atmosphere

2: triethylamine / acetonitrile / 0 - 20 °C / Inert atmosphere

3: 1,8-diazabicyclo[5.4.0]undec-7-ene / methanol; toluene / 52 h / 20 °C / Inert atmosphere

4: lithium borohydride / ethanol

5: 1-methyl-pyrrolidin-2-one / N,N-dimethyl-formamide / 72 h / 100 °C

6: 1-dodecylthiol; sodium hydroxide / methanol; acetonitrile / 1.5 h / 50 °C / Inert atmosphere

7: acetonitrile / 20 - 50 °C / Inert atmosphere

With 1-methyl-pyrrolidin-2-one; dmap; lithium borohydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; sodium hydroxide; 1-dodecylthiol; In methanol; ethanol; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1021/acs.oprd.1c00098

upstream raw materials:

(2S,5R)-5-hydroxypiperidine-2-carboxylic acid

oxalic acid

5-hydroxypiperidine-2-carboxylic acid