(RS)-1-(Benzyloxycarbonyl)-1,8-diaza-7-oxospiro<5.4>decane-8-acetic acid methyl ester

Base Information

• Chemical Name: (RS)-1-(Benzyloxycarbonyl)-1,8-diaza-7-oxospiro<5.4>decane-8-acetic acid methyl ester
• CAS No.: 146691-54-5
• Molecular Formula: C₁₉H₂₄N₂O₅
• Molecular Weight: 360.41
• Mol file: 146691-54-5.mol

Synonyms:(RS)-1-(Benzyloxycarbonyl)-1,8-diaza-7-oxospiro<5.4>decane-8-acetic acid methyl ester

Chemical Property of (RS)-1-(Benzyloxycarbonyl)-1,8-diaza-7-oxospiro<5.4>decane-8-acetic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (RS)-1-(Benzyloxycarbonyl)-1,8-diaza-7-oxospiro<5.4>decane-8-acetic acid methyl ester

There total 12 articles about (RS)-1-(Benzyloxycarbonyl)-1,8-diaza-7-oxospiro<5.4>decane-8-acetic acid methyl ester 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: 60.0%

Methyl N-(benzyloxycarbonyl)-2(RS)-(hydroxyethyl)pipecolylglycinate (146691-53-4) → (RS)-1-(Benzyloxycarbonyl)-1,8-diaza-7-oxospiro<5.4>decane-8-acetic acid methyl ester (146691-54-5)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; for 2h; Ambient temperature;

DOI:10.1021/jo00056a018

Reference yield:

N-(benzyloxycarbonyl)-DL-pipecolinic acid tert-butyl ester (71170-89-3) → (RS)-1-(Benzyloxycarbonyl)-1,8-diaza-7-oxospiro<5.4>decane-8-acetic acid methyl ester (146691-54-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) LDA / 1.) THF, hexane, EtPh, -78 deg C, 20 min, 2.) -78 deg C, 20 min

2: CF₃CO₂H / CH₂Cl₂ / 3 h / Ambient temperature

3: HOBt, NEt₃, dicyclohexylcarbodiimide (DCC) / CHCl₃ / Ambient temperature

4: 1.) OsO₄, H₂O, 2.) NaIO₄ / 1.) MeOH, 10 min, room temperature, 2.) 2 h

5: NaBH₄ / ethyl acetate; propan-2-ol / 1 h / -78 °C

6: 60 percent / Ph₃P, diethyl azodicarboxylate (DEAD) / tetrahydrofuran / 2 h / Ambient temperature

With sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; water; benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; triphenylphosphine; trifluoroacetic acid; lithium diisopropyl amide; diethylazodicarboxylate; In tetrahydrofuran; dichloromethane; chloroform; ethyl acetate; isopropyl alcohol;

DOI:10.1021/jo00056a018

Reference yield:

N-benzyloxycarbonyl D/L-pipecolinic acid (28697-07-6) → (RS)-1-(Benzyloxycarbonyl)-1,8-diaza-7-oxospiro<5.4>decane-8-acetic acid methyl ester (146691-54-5)

Guidance literature:

Multi-step reaction with 7 steps

1: 58 percent / H₂SO₄ / diethyl ether / 24 h / Ambient temperature

2: 1.) LDA / 1.) THF, hexane, EtPh, -78 deg C, 20 min, 2.) -78 deg C, 20 min

3: CF₃CO₂H / CH₂Cl₂ / 3 h / Ambient temperature

4: HOBt, NEt₃, dicyclohexylcarbodiimide (DCC) / CHCl₃ / Ambient temperature

5: 1.) OsO₄, H₂O, 2.) NaIO₄ / 1.) MeOH, 10 min, room temperature, 2.) 2 h

6: NaBH₄ / ethyl acetate; propan-2-ol / 1 h / -78 °C

7: 60 percent / Ph₃P, diethyl azodicarboxylate (DEAD) / tetrahydrofuran / 2 h / Ambient temperature

With sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; sulfuric acid; water; benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; triphenylphosphine; trifluoroacetic acid; lithium diisopropyl amide; diethylazodicarboxylate; In tetrahydrofuran; diethyl ether; dichloromethane; chloroform; ethyl acetate; isopropyl alcohol;

DOI:10.1021/jo00056a018

upstream raw materials:

2-[2-(Methoxycarbonylmethyl-amino)-ethyl]-piperidine-1,2-dicarboxylic acid 1-benzyl ester

Methyl N-(benzyloxycarbonyl)-2(RS)-(hydroxyethyl)pipecolylglycinate

N-(benzyloxycarbonyl)-DL-pipecolinic acid tert-butyl ester

N-benzyloxycarbonyl D/L-pipecolinic acid