(-)-tert-butyl (2S,3R)-3-[(2E)-2-(benzyloxycarbonylmethylene)pyrrolidin-1-yl]-2-ethylhexanoate

Base Information

• Chemical Name: (-)-tert-butyl (2S,3R)-3-[(2E)-2-(benzyloxycarbonylmethylene)pyrrolidin-1-yl]-2-ethylhexanoate
• CAS No.: 850453-61-1
• Molecular Formula: C₂₅H₃₇NO₄
• Molecular Weight: 415.573
• Mol file: 850453-61-1.mol

Synonyms:(-)-tert-butyl (2S,3R)-3-[(2E)-2-(benzyloxycarbonylmethylene)pyrrolidin-1-yl]-2-ethylhexanoate

Chemical Property of (-)-tert-butyl (2S,3R)-3-[(2E)-2-(benzyloxycarbonylmethylene)pyrrolidin-1-yl]-2-ethylhexanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-tert-butyl (2S,3R)-3-[(2E)-2-(benzyloxycarbonylmethylene)pyrrolidin-1-yl]-2-ethylhexanoate

There total 3 articles about (-)-tert-butyl (2S,3R)-3-[(2E)-2-(benzyloxycarbonylmethylene)pyrrolidin-1-yl]-2-ethylhexanoate 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: 81.0%

(-)-tert-butyl (2S,3R)-3-(2-thioxopyrrolidin-1-yl)-2-ethylhexanoate (850453-59-7) + Benzyl bromoacetate (5437-45-6) → (-)-tert-butyl (2S,3R)-3-[(2E)-2-(benzyloxycarbonylmethylene)pyrrolidin-1-yl]-2-ethylhexanoate (850453-61-1)

Guidance literature:

(-)-tert-butyl (2S,3R)-3-(2-thioxopyrrolidin-1-yl)-2-ethylhexanoate; Benzyl bromoacetate; In acetonitrile; at 20 ℃; for 18h;

With triethylamine; triphenylphosphine; In acetonitrile; at 20 ℃;

DOI:10.1039/b418062c

Reference yield:

tert-butyl (-)-(2S,3R)-3-(2-oxopyrrolidin-1-yl)-2-ethylhexanoate (850453-64-4) → (-)-tert-butyl (2S,3R)-3-[(2E)-2-(benzyloxycarbonylmethylene)pyrrolidin-1-yl]-2-ethylhexanoate (850453-61-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 95 percent / Lawesson's reagent / toluene / 18 h / Heating

2.1: acetonitrile / 18 h / 20 °C

2.2: 81 percent / PPh₃; Et₃N / acetonitrile / 20 °C

With Lawessons reagent; In toluene; acetonitrile;

DOI:10.1039/b418062c

Reference yield:

tert-butyl (3R)-3-[N-(4-chloro-1-oxo)butyl]amino-2-ethylhexanoate → (-)-tert-butyl (2S,3R)-3-[(2E)-2-(benzyloxycarbonylmethylene)pyrrolidin-1-yl]-2-ethylhexanoate (850453-61-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 270 mg / t-BuOK / 2-methyl-propan-2-ol / 36 h / 20 °C

2.1: 95 percent / Lawesson's reagent / toluene / 18 h / Heating

3.1: acetonitrile / 18 h / 20 °C

3.2: 81 percent / PPh₃; Et₃N / acetonitrile / 20 °C

With Lawessons reagent; potassium tert-butylate; In toluene; acetonitrile; tert-butyl alcohol;

DOI:10.1039/b418062c

upstream raw materials:

(-)-tert-butyl (2S,3R)-3-(2-thioxopyrrolidin-1-yl)-2-ethylhexanoate

Benzyl bromoacetate

tert-butyl (-)-(2S,3R)-3-(2-oxopyrrolidin-1-yl)-2-ethylhexanoate

Downstream raw materials:

(+)-benzyl (5R,6R)-6-ethyl-7-oxo-5-propyl-1,2,3,5,6,7-hexahydroindolizine-8-carboxylate