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

Base Information

• Chemical Name: Methyl N-(benzyloxycarbonyl)-2(RS)-(hydroxyethyl)pipecolylglycinate
• CAS No.: 146691-53-4
• Molecular Formula: C₁₉H₂₆N₂O₆
• Molecular Weight: 378.425
• Mol file: 146691-53-4.mol

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

Chemical Property of Methyl N-(benzyloxycarbonyl)-2(RS)-(hydroxyethyl)pipecolylglycinate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Methyl N-(benzyloxycarbonyl)-2(RS)-(hydroxyethyl)pipecolylglycinate

There total 8 articles about Methyl N-(benzyloxycarbonyl)-2(RS)-(hydroxyethyl)pipecolylglycinate 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-(Methoxycarbonylmethyl-carbamoyl)-2-(2-oxo-ethyl)-piperidine-1-carboxylic acid benzyl ester (1026155-18-9) → Methyl N-(benzyloxycarbonyl)-2(RS)-(hydroxyethyl)pipecolylglycinate (146691-53-4)

Guidance literature:

With sodium tetrahydroborate; In ethyl acetate; isopropyl alcohol; at -78 ℃; for 1h; Yield given;

DOI:10.1021/jo00056a018

Reference yield:

N-(benzyloxycarbonyl)-DL-pipecolinic acid tert-butyl ester (71170-89-3) → Methyl N-(benzyloxycarbonyl)-2(RS)-(hydroxyethyl)pipecolylglycinate (146691-53-4)

Guidance literature:

Multi-step reaction with 5 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

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

DOI:10.1021/jo00056a018

Reference yield:

N-benzyloxycarbonyl D/L-pipecolinic acid (28697-07-6) → Methyl N-(benzyloxycarbonyl)-2(RS)-(hydroxyethyl)pipecolylglycinate (146691-53-4)

Guidance literature:

Multi-step reaction with 6 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

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

DOI:10.1021/jo00056a018

upstream raw materials:

2-(Methoxycarbonylmethyl-carbamoyl)-2-(2-oxo-ethyl)-piperidine-1-carboxylic acid benzyl ester

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

N-benzyloxycarbonyl D/L-pipecolinic acid

benzyl chloroformate

Downstream raw materials:

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