(2S,4S)-N-tert-butyloxycarbonyl-4-propylproline

Base Information

• Chemical Name: (2S,4S)-N-tert-butyloxycarbonyl-4-propylproline
• CAS No.: 540501-62-0
• Molecular Formula: C₁₃H₂₃NO₄
• Molecular Weight: 257.33
• Mol file: 540501-62-0.mol

Synonyms:

Chemical Property of (2S,4S)-N-tert-butyloxycarbonyl-4-propylproline

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,4S)-N-tert-butyloxycarbonyl-4-propylproline

There total 17 articles about (2S,4S)-N-tert-butyloxycarbonyl-4-propylproline 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: 67.0%

1-tert-butyl 2-methyl (2S,4S)-4-propyl-1,2-pyrrolidinedicarboxylate (934470-75-4) → (2S,4S)-N-tert-butyloxycarbonyl-4-propylproline (540501-62-0)

Guidance literature:

With sodium hydroxide; In methanol; water; at 20 ℃; for 6h;

DOI:10.1016/j.bmc.2007.01.033

Reference yield:

(2S,4R)-(N-tert-butyloxycarbonyl)-4-(Z)-propenylproline (802911-23-5) → (2S,4S)-N-tert-butyloxycarbonyl-4-propylproline (540501-62-0)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethyl acetate; at 20 ℃; for 15h; ambient pressure;

DOI:10.1002/chem.200400406

Reference yield:

2-(tert-butyl-dimethyl-silanyloxymethyl)-4-propyl-pyrrolidine-1-carboxylic acid tert-butyl ester → (2S,4R)-N-tert-butyloxycarbonyl-4-propylproline (540501-47-1) + (2S,4S)-N-tert-butyloxycarbonyl-4-propylproline (540501-62-0)

Guidance literature:

2-(tert-butyl-dimethyl-silanyloxymethyl)-4-propyl-pyrrolidine-1-carboxylic acid tert-butyl ester; With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 6h;

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium chlorite; NaH₂PO₄ buffer; sodium hypochlorite; In water; acetonitrile; at 45 ℃; for 24h; pH=6.6; Title compound not separated from byproducts;

DOI:10.1021/jo034214l

upstream raw materials:

(2S,4R)-(N-tert-butyloxycarbonyl)-4-(Z)-propenylproline

1-tert-butyl 2-methyl (2S,4S)-4-propyl-1,2-pyrrolidinedicarboxylate

1-tert-butyl 2-methyl (2S,4S)-4-allyl-1,2-pyrrolidinedicarboxylate

di-tert-butyl dicarbonate

Refernces

• 1、 Zlatopolskiy, Boris D.,Loscha, Karin,Alvermann, Petra,Kozhushkov, Sergei I.,Nikolaev, Sergej V.,Zeeck, Axel,De Meijere, Armin. "Final elucidation of the absolute configuration of the signal metabolite hormaomycin". . p. 4708 - 4717. Retrieved 2007/10/03.