(2R,3S)-1-Benzyl-3-hydroxy-6-oxo-piperidine-2-carboxylic acid ethyl ester

Base Information

• Chemical Name: (2R,3S)-1-Benzyl-3-hydroxy-6-oxo-piperidine-2-carboxylic acid ethyl ester
• CAS No.: 165672-46-8
• Molecular Formula: C₁₅H₁₉NO₄
• Molecular Weight: 277.32
• Mol file: 165672-46-8.mol

Synonyms:(2R,3S)-1-Benzyl-3-hydroxy-6-oxo-piperidine-2-carboxylic acid ethyl ester

Chemical Property of (2R,3S)-1-Benzyl-3-hydroxy-6-oxo-piperidine-2-carboxylic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S)-1-Benzyl-3-hydroxy-6-oxo-piperidine-2-carboxylic acid ethyl ester

There total 1 articles about (2R,3S)-1-Benzyl-3-hydroxy-6-oxo-piperidine-2-carboxylic acid ethyl 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: 88.0%

ethyl 1-benzyl-3,6-dioxo-2-piperidinecarboxylate (92912-21-5) → (2R,3S)-1-Benzyl-3-hydroxy-6-oxo-piperidine-2-carboxylic acid ethyl ester (165672-46-8)

Guidance literature:

With baker's yeast; In water;

DOI:10.1021/jo990397t

Reference yield: 98.0%

chloromethyl methyl ether (107-30-2) + (2R,3S)-1-Benzyl-3-hydroxy-6-oxo-piperidine-2-carboxylic acid ethyl ester (165672-46-8) → (2R,3S)-1-benzyl-3-methoxymethoxy-6-oxopiperidine-2-carboxylic acid ethyl ester (165672-48-0)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In chloroform; Heating;

DOI:10.1016/0040-4039(95)00661-U DOI:10.1021/jo990397t

Reference yield:

(2R,3S)-1-Benzyl-3-hydroxy-6-oxo-piperidine-2-carboxylic acid ethyl ester (165672-46-8) → (2S,3S,6S)-2-Benzyloxymethyl-3-hydroxy-6-methoxycarbonylmethyl-piperidine-1-carboxylic acid methyl ester (239802-21-2)

Guidance literature:

Multi-step reaction with 10 steps

1: 98 percent / Huenig base / CHCl₃ / Heating

2: 96 percent / Super-Hydride / tetrahydrofuran / 0 °C

3: 95 percent / n-Bu₃P, pyridine

4: 95 percent / Raney Ni (W-4) / ethanol

5: conc. HCl / methanol

6: 96 percent / NaH / dimethylformamide; benzene

7: 90 percent / Lawesson's reagent / tetrahydrofuran / Heating

8: 53 percent / PPh₃, Et₃N / acetonitrile / Heating

9: H₂ / Pd(OH)2 / methanol

10: K₂CO₃

With Lawessons reagent; pyridine; hydrogenchloride; tributylphosphine; Raney Ni (W-4); hydrogen; sodium hydride; lithium triethylborohydride; potassium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; palladium dihydroxide; In tetrahydrofuran; methanol; ethanol; chloroform; N,N-dimethyl-formamide; acetonitrile; benzene;

DOI:10.1021/jo990397t

upstream raw materials:

ethyl 1-benzyl-3,6-dioxo-2-piperidinecarboxylate

Downstream raw materials:

(2R,3S)-1-benzyl-3-methoxymethoxy-6-oxopiperidine-2-carboxylic acid ethyl ester

(5R,6S)-1-Benzyl-5-hydroxy-6-hydroxymethyl-piperidin-2-one

(5S,6S)-1-Benzyl-5-methoxymethoxy-6-methyl-piperidin-2-one

(2S,3S,6R)-3-Benzyloxy-6-(2-hydroxy-ethyl)-2-methyl-piperidine-1-carboxylic acid methyl ester