N-benzyloxycarbonyl-(2S,5S)-5-hydroxypipecolic acid tert-butyl ester

Base Information

• Chemical Name: N-benzyloxycarbonyl-(2S,5S)-5-hydroxypipecolic acid tert-butyl ester
• CAS No.: 169825-97-2
• Molecular Formula: C₁₈H₂₅NO₅
• Molecular Weight: 335.4
• Mol file: 169825-97-2.mol

Synonyms:N-benzyloxycarbonyl-(2S,5S)-5-hydroxypipecolic acid tert-butyl ester

Chemical Property of N-benzyloxycarbonyl-(2S,5S)-5-hydroxypipecolic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

Useful:

Technology Process of N-benzyloxycarbonyl-(2S,5S)-5-hydroxypipecolic acid tert-butyl ester

There total 3 articles about N-benzyloxycarbonyl-(2S,5S)-5-hydroxypipecolic acid tert-butyl 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: 91.0%

(2S)-5-oxopiperidine-1,2-dicarboxylic acid 1-benzyl ester 2-tert-butyl ester (147489-30-3) → N-benzyloxycarbonyl-(2S,5S)-5-hydroxypipecolic acid tert-butyl ester (169825-97-2)

Guidance literature:

With sodium tetrahydroborate; ethanol; for 0.333333h; Product distribution / selectivity; Cooling with ice;

Reference yield: 22.0%

(2S)-5-oxopiperidine-1,2-dicarboxylic acid 1-benzyl ester 2-tert-butyl ester (147489-30-3) → N-benzyloxycarbonyl-(2S,5R)-5-hydroxypipecolic acid tert-butyl ester + N-benzyloxycarbonyl-(2S,5S)-5-hydroxypipecolic acid tert-butyl ester (169825-97-2)

Guidance literature:

With L-Selectride; In tetrahydrofuran; at -45 - 20 ℃; for 0.5h;

DOI:10.1039/c0mb00227e

Reference yield:

tert-butyl N-benzyloxycarbonyl-L-pyroglutamate (81470-51-1) → N-benzyloxycarbonyl-(2S,5S)-5-hydroxypipecolic acid tert-butyl ester (169825-97-2)

Guidance literature:

Multi-step reaction with 3 steps

1: potassium tert-butylate / N,N-dimethyl-formamide / 1.33 h / 5 °C / Inert atmosphere

2: bis(1,5-cyclooctadiene)diiridium(I) dichloride / 1,2-dichloro-ethane / 2 h / 70 °C / Inert atmosphere

3: ethanol; sodium tetrahydroborate / 0.33 h / Cooling with ice

With sodium tetrahydroborate; ethanol; potassium tert-butylate; bis(1,5-cyclooctadiene)diiridium(I) dichloride; In 1,2-dichloro-ethane; N,N-dimethyl-formamide;

upstream raw materials:

(2S)-5-oxopiperidine-1,2-dicarboxylic acid 1-benzyl ester 2-tert-butyl ester

tert-butyl N-benzyloxycarbonyl-L-pyroglutamate

Downstream raw materials:

(2S,5S)-N-[(benzyloxy)carbonyl]-5-hydroxy-2-piperidinecarboxylic acid

benzyl (1S,4S)-5-aza-2-oxa-3-oxobicyclo[2.2.2]octane-5-carboxylate

N-Cbz-5-(S)-dibenzylphosphate-(S)-pipecolic acid

N-Cbz-5-(S)-dibenzylphosphate-(S)-tert-butylpipecolate