(2S,1′S)-2-(1′-hydroxybut-3′-en-1′-yl)-1-(carbobenzyloxy)pyrrolidine

Base Information

• Chemical Name: (2S,1′S)-2-(1′-hydroxybut-3′-en-1′-yl)-1-(carbobenzyloxy)pyrrolidine
• CAS No.: 123411-88-1
• Molecular Formula: C₁₆H₂₁NO₃
• Molecular Weight: 275.348
• Mol file: 123411-88-1.mol

Synonyms:(2S,1′S)-2-(1′-hydroxybut-3′-en-1′-yl)-1-(carbobenzyloxy)pyrrolidine

Chemical Property of (2S,1′S)-2-(1′-hydroxybut-3′-en-1′-yl)-1-(carbobenzyloxy)pyrrolidine

Chemical Property:

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Technology Process of (2S,1′S)-2-(1′-hydroxybut-3′-en-1′-yl)-1-(carbobenzyloxy)pyrrolidine

There total 1 articles about (2S,1′S)-2-(1′-hydroxybut-3′-en-1′-yl)-1-(carbobenzyloxy)pyrrolidine 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: 80.0%

(S)-2-formylpyrrolidine-1-carboxylic acid benzyl ester (71461-30-8) + allyl bromide (106-95-6) → (2S,1′R)-2-(1′-hydroxybut-3′-en-1′-yl)-1-(carbobenzyloxy)pyrrolidine (123411-87-0) + (2S,1′S)-2-(1′-hydroxybut-3′-en-1′-yl)-1-(carbobenzyloxy)pyrrolidine (123411-88-1)

Guidance literature:

With ammonium chloride; zinc; In tetrahydrofuran; water; at 0 - 20 ℃; for 2h;

DOI:10.1055/s-0037-1609582

Reference yield: 50.0%

(2S,1′S)-2-(1′-hydroxybut-3′-en-1′-yl)-1-(carbobenzyloxy)pyrrolidine (123411-88-1) → (2S,1′R)-2-(3′,4′-epoxy-1′-hydroxbut-1′-yl)-1-(carbobenzyloxy)pyrrolidine

Guidance literature:

With titanium(IV) isopropylate; tert.-butylhydroperoxide; 3 A molecular sieve; In dichloromethane; at -15 ℃;

DOI:10.1016/S0957-4166(02)00511-6

Reference yield:

(2S,1′S)-2-(1′-hydroxybut-3′-en-1′-yl)-1-(carbobenzyloxy)pyrrolidine (123411-88-1) → (2S,1′S,3′S)-2-(3′,4′-epoxy-1′-hydroxbut-1′-yl)-1-(carbobenzyloxy)pyrrolidine + (2S,1′S,3′R)-2-(3′,4′-epoxy-1′-hydroxbut-1′-yl)-1-(carbobenzyloxy)pyrrolidine

Guidance literature:

With tert.-butylhydroperoxide; bis(acetylacetonate)oxovanadium; In dichloromethane; at 20 ℃; for 20h; Reagent/catalyst; Overall yield = 55 %; Inert atmosphere;

DOI:10.1055/s-0037-1609582

upstream raw materials:

(S)-2-formylpyrrolidine-1-carboxylic acid benzyl ester

allyl bromide