bis<<3-benzyloxycarbonyl-2-oxa-3-azabicyclo<2.2.2>-oct-5-en-1-yl>methyl>amine

Base Information

• Chemical Name: bis<<3-benzyloxycarbonyl-2-oxa-3-azabicyclo<2.2.2>-oct-5-en-1-yl>methyl>amine
• CAS No.: 96657-47-5
• Molecular Formula: C₃₀H₃₃N₃O₆
• Molecular Weight: 531.609
• Mol file: 96657-47-5.mol

Synonyms:

Chemical Property of bis<<3-benzyloxycarbonyl-2-oxa-3-azabicyclo<2.2.2>-oct-5-en-1-yl>methyl>amine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of bis<<3-benzyloxycarbonyl-2-oxa-3-azabicyclo<2.2.2>-oct-5-en-1-yl>methyl>amine

There total 5 articles about bis<<3-benzyloxycarbonyl-2-oxa-3-azabicyclo<2.2.2>-oct-5-en-1-yl>methyl>amine 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: 28.0%

3-benzyloxycarbonyl-2-oxa-3-azabicyclo<2.2.2>oct-5-ene-1-carbaldehyde (96657-46-4) → bis<<3-benzyloxycarbonyl-2-oxa-3-azabicyclo<2.2.2>-oct-5-en-1-yl>methyl>amine (96657-47-5,96688-21-0)

Guidance literature:

With ammonium acetate; 3 A molecular sieve; sodium cyanoborohydride; In methanol; for 168h; Ambient temperature;

DOI:10.1016/S0040-4020(01)88799-8

Reference yield:

Benzyl N-hydroxycarbamate (3426-71-9) → bis<<3-benzyloxycarbonyl-2-oxa-3-azabicyclo<2.2.2>-oct-5-en-1-yl>methyl>amine (96657-47-5,96688-21-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 93 percent / tetraethylammonium periodate / CH₂Cl₂ / 1.33 h / -7 - -3 °C

2: 100 percent / sodium borohydride / methanol / 0.08 h

3: 1.) N,N'-dicyclohexylcarbodiimide, pyridine, trifluoroacetic acid; 2.) oxalic acid / 1.) dimethylsulphoxide, benzene, RT, 18 h; 2.) MeOH, 1 h

4: 28 percent / molecular sieves 3A, ammonium acetate, sodium cyanoborohydride / methanol / 168 h / Ambient temperature

With pyridine; ammonium acetate; sodium tetrahydroborate; 3 A molecular sieve; oxalic acid; sodium cyanoborohydride; tetraethylammonium metaperiodate; dicyclohexyl-carbodiimide; trifluoroacetic acid; In methanol; dichloromethane;

DOI:10.1016/S0040-4020(01)88799-8

Reference yield:

ethyl 1,3-cyclohexadiene-1-carboxylate (3725-40-4) → bis<<3-benzyloxycarbonyl-2-oxa-3-azabicyclo<2.2.2>-oct-5-en-1-yl>methyl>amine (96657-47-5,96688-21-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 93 percent / tetraethylammonium periodate / CH₂Cl₂ / 1.33 h / -7 - -3 °C

2: 100 percent / sodium borohydride / methanol / 0.08 h

3: 1.) N,N'-dicyclohexylcarbodiimide, pyridine, trifluoroacetic acid; 2.) oxalic acid / 1.) dimethylsulphoxide, benzene, RT, 18 h; 2.) MeOH, 1 h

4: 28 percent / molecular sieves 3A, ammonium acetate, sodium cyanoborohydride / methanol / 168 h / Ambient temperature

With pyridine; ammonium acetate; sodium tetrahydroborate; 3 A molecular sieve; oxalic acid; sodium cyanoborohydride; tetraethylammonium metaperiodate; dicyclohexyl-carbodiimide; trifluoroacetic acid; In methanol; dichloromethane;

DOI:10.1016/S0040-4020(01)88799-8

upstream raw materials:

3-benzyloxycarbonyl-2-oxa-3-azabicyclo<2.2.2>oct-5-ene-1-carbaldehyde

Benzyl N-hydroxycarbamate

ethyl 1,3-cyclohexadiene-1-carboxylate

ethyl 3-benzyloxycarbonyl-2-oxa-3-azabicyclo<2.2.2>oct-5-ene-1-carboxylate