benzyl 9-(2-ethylenedioxyethyl)-1,4-dioxa-7-azaspiro<4.5>decane-7-carboxylate

Base Information

• Chemical Name: benzyl 9-(2-ethylenedioxyethyl)-1,4-dioxa-7-azaspiro<4.5>decane-7-carboxylate
• CAS No.: 76525-55-8
• Molecular Formula: C₁₉H₂₅NO₆
• Molecular Weight: 363.411
• Mol file: 76525-55-8.mol

Synonyms:benzyl 9-(2-ethylenedioxyethyl)-1,4-dioxa-7-azaspiro<4.5>decane-7-carboxylate

Chemical Property of benzyl 9-(2-ethylenedioxyethyl)-1,4-dioxa-7-azaspiro<4.5>decane-7-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl 9-(2-ethylenedioxyethyl)-1,4-dioxa-7-azaspiro<4.5>decane-7-carboxylate

There total 7 articles about benzyl 9-(2-ethylenedioxyethyl)-1,4-dioxa-7-azaspiro<4.5>decane-7-carboxylate 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: 94.0%

9-(2-ethylenedioxyethyl)-1,4-dioxa-7-azaspiro<4.5>decane (76525-56-9) + benzyl chloroformate (501-53-1,94274-21-2) → benzyl 9-(2-ethylenedioxyethyl)-1,4-dioxa-7-azaspiro<4.5>decane-7-carboxylate (76525-55-8)

Guidance literature:

With triethylamine; In diethyl ether; for 1h; Ambient temperature;

DOI:10.1248/cpb.30.4052

Reference yield:

(+/-)-1-(ethoxycarbonyl)-1,2,3,6-tetrahydro-3-pyridone (66643-50-3) → benzyl 9-(2-ethylenedioxyethyl)-1,4-dioxa-7-azaspiro<4.5>decane-7-carboxylate (76525-55-8)

Guidance literature:

Multi-step reaction with 6 steps

1: 23 percent / cuprous chloride / tetrahydrofuran / 1 h / -50 °C

2: 69 percent / p-toluenesulfonic acid / benzene / Heating

4: 86 percent / p-toluenesulfonic acid / benzene / 20 h / Heating

5: 79 percent / KOH / H₂O; ethanol / 36 h / Heating

6: 94 percent / Et₃N / diethyl ether / 1 h / Ambient temperature

With potassium hydroxide; toluene-4-sulfonic acid; triethylamine; copper(l) chloride; In tetrahydrofuran; diethyl ether; ethanol; water; benzene;

DOI:10.1248/cpb.30.4052

Reference yield:

ethyl 3-hydroxy-1,2,3,6-tetrahydropiperidine-1-carboxylate (66643-49-0) → benzyl 9-(2-ethylenedioxyethyl)-1,4-dioxa-7-azaspiro<4.5>decane-7-carboxylate (76525-55-8)

Guidance literature:

Multi-step reaction with 7 steps

1: mercuric acetate / 48 h / 200 °C

2: p-toluenesulfonic acid / 1 h / Heating

3: 1.) BF₃-etherate, NaBH₄; 2.) H₂O₂, 3N NaOH / 1.) THF, ice cooling, 3 h; 2.) 2 h

4: 91 percent / pyridinium chlorochromate (PCC), NaOAc / CH₂Cl₂ / 24 h / Ambient temperature

5: 86 percent / p-toluenesulfonic acid / benzene / 20 h / Heating

6: 79 percent / KOH / H₂O; ethanol / 36 h / Heating

7: 94 percent / Et₃N / diethyl ether / 1 h / Ambient temperature

With potassium hydroxide; sodium hydroxide; sodium tetrahydroborate; boron trifluoride diethyl etherate; mercury(II) diacetate; dihydrogen peroxide; sodium acetate; toluene-4-sulfonic acid; triethylamine; pyridinium chlorochromate; In diethyl ether; ethanol; dichloromethane; water; benzene;

DOI:10.1248/cpb.30.4052

upstream raw materials:

9-(2-ethylenedioxyethyl)-1,4-dioxa-7-azaspiro<4.5>decane

benzyl chloroformate

(+/-)-1-(ethoxycarbonyl)-1,2,3,6-tetrahydro-3-pyridone

ethyl 3-hydroxy-1,2,3,6-tetrahydropiperidine-1-carboxylate

Downstream raw materials:

benzyl 9-(2-oxoethyl)-1,4-dioxa-7-azaspiro<4.5>decane-7-carboxylate

(1R,4S)-6-Hydroxy-7-oxo-2-aza-bicyclo[2.2.2]octane-2-carboxylic acid benzyl ester

6-Hydroxy-7-oxo-2-aza-bicyclo[2.2.2]octane-2-carboxylic acid benzyl ester

benzyl 7-hydroxy-6-oxo-2-azabicyclo<2.2.2>octane-2-carboxylate