(2S,3S)-3-Vinyl-piperidine-1,2-dicarboxylic acid 2-(2-chloro-2-phenyl-ethyl) ester 1-vinyl ester

Base Information

• Chemical Name: (2S,3S)-3-Vinyl-piperidine-1,2-dicarboxylic acid 2-(2-chloro-2-phenyl-ethyl) ester 1-vinyl ester
• CAS No.: 213685-94-0
• Molecular Formula: C₁₉H₂₂ClNO₄
• Molecular Weight: 363.841
• Mol file: 213685-94-0.mol

Synonyms:

Chemical Property of (2S,3S)-3-Vinyl-piperidine-1,2-dicarboxylic acid 2-(2-chloro-2-phenyl-ethyl) ester 1-vinyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S)-3-Vinyl-piperidine-1,2-dicarboxylic acid 2-(2-chloro-2-phenyl-ethyl) ester 1-vinyl ester

There total 6 articles about (2S,3S)-3-Vinyl-piperidine-1,2-dicarboxylic acid 2-(2-chloro-2-phenyl-ethyl) ester 1-vinyl 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: 40.0%

Vinyl chloroformate (5130-24-5) + (4R,9S,9aS)-4-phenyl-9-vinyloctahydropyrido[2,1-c][1,4]oxazin-1-one (213685-93-9) → (2S,3S)-3-Vinyl-piperidine-1,2-dicarboxylic acid 2-(2-chloro-2-phenyl-ethyl) ester 1-vinyl ester (213685-94-0)

Guidance literature:

In dichloromethane; for 240h; Heating;

DOI:10.1016/S0040-4020(98)00486-4

Reference yield:

D-2-phenylglycinol (56613-80-0) → (2S,3S)-3-Vinyl-piperidine-1,2-dicarboxylic acid 2-(2-chloro-2-phenyl-ethyl) ester 1-vinyl ester (213685-94-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 70 percent / (i-Pr)2NH / acetonitrile / 240 h / Heating

2: 45 percent / CF₃CO₂H / tetrahydrofuran; H₂O / 120 h / 0 - 20 °C

3: 98 percent / n-Bu₄NF / tetrahydrofuran / 24 h / Heating

4: 70 percent / DMSO; oxalyl chloride; Et₃N / CH₂Cl₂ / 2.5 h / -50 - 20 °C

5: 40 percent / CH₂Cl₂ / 240 h / Heating

With oxalyl dichloride; tetrabutyl ammonium fluoride; dimethyl sulfoxide; triethylamine; diisopropylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; water; acetonitrile; 1: Substitution / 2: Condensation / 3: Ring cleavage / 4: Swern oxidation / 5: Ring cleavage;

DOI:10.1016/S0040-4020(98)00486-4

Reference yield:

(Z)-6-(trimethylsilyl)hex-4-enyl methanesulfonate (97997-96-1) → (2S,3S)-3-Vinyl-piperidine-1,2-dicarboxylic acid 2-(2-chloro-2-phenyl-ethyl) ester 1-vinyl ester (213685-94-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 70 percent / (i-Pr)2NH / acetonitrile / 240 h / Heating

2: 45 percent / CF₃CO₂H / tetrahydrofuran; H₂O / 120 h / 0 - 20 °C

3: 98 percent / n-Bu₄NF / tetrahydrofuran / 24 h / Heating

4: 70 percent / DMSO; oxalyl chloride; Et₃N / CH₂Cl₂ / 2.5 h / -50 - 20 °C

5: 40 percent / CH₂Cl₂ / 240 h / Heating

With oxalyl dichloride; tetrabutyl ammonium fluoride; dimethyl sulfoxide; triethylamine; diisopropylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; water; acetonitrile; 1: Substitution / 2: Condensation / 3: Ring cleavage / 4: Swern oxidation / 5: Ring cleavage;

DOI:10.1016/S0040-4020(98)00486-4

upstream raw materials:

Vinyl chloroformate

(4R,9S,9aS)-4-phenyl-9-vinyloctahydropyrido[2,1-c][1,4]oxazin-1-one

D-2-phenylglycinol

(Z)-6-(trimethylsilyl)hex-4-enyl methanesulfonate

Refernces