benzyl (2S,2αS,5R)-(-)-5-allyl-2-(1-hydroxybutyl)pyrrolidine-1-carboxylate

Base Information

• Chemical Name: benzyl (2S,2αS,5R)-(-)-5-allyl-2-(1-hydroxybutyl)pyrrolidine-1-carboxylate
• CAS No.: 1437682-39-7
• Molecular Formula: C₁₉H₂₇NO₃
• Molecular Weight: 317.428
• Mol file: 1437682-39-7.mol

Synonyms:benzyl (2S,2αS,5R)-(-)-5-allyl-2-(1-hydroxybutyl)pyrrolidine-1-carboxylate

Chemical Property of benzyl (2S,2αS,5R)-(-)-5-allyl-2-(1-hydroxybutyl)pyrrolidine-1-carboxylate

Chemical Property:

Purity/Quality:

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Technology Process of benzyl (2S,2αS,5R)-(-)-5-allyl-2-(1-hydroxybutyl)pyrrolidine-1-carboxylate

There total 7 articles about benzyl (2S,2αS,5R)-(-)-5-allyl-2-(1-hydroxybutyl)pyrrolidine-1-carboxylate 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: 94.0%

benzyl (2S,5R)-(-)-5-allyl-2-butyrylpyrrolidine-1-carboxylate (1437682-43-3) → benzyl (2S,2αS,5R)-(-)-5-allyl-2-(1-hydroxybutyl)pyrrolidine-1-carboxylate (1437682-39-7)

Guidance literature:

With sodium tetrahydroborate; In methanol; at 0 - 20 ℃; for 22h; stereoselective reaction;

DOI:10.1002/ejoc.201200974

Reference yield: 80.0%

benzyl (2S,5R)-(-)-5-allyl-2-butyrylpyrrolidine-1-carboxylate (1437682-43-3) → benzyl (2S,2αS,5R)-(-)-5-allyl-2-(1-hydroxybutyl)pyrrolidine-1-carboxylate (1437682-39-7) + benzyl (2S,2αR,5R)-(-)-5-allyl-2-(1-hydroxybutyl)pyrrolidine-1-carboxylate (1437682-41-1)

Guidance literature:

benzyl (2S,5R)-(-)-5-allyl-2-butyrylpyrrolidine-1-carboxylate; With cerium(III) chloride heptahydrate; In methanol; at 0 ℃; for 0.166667h;

With sodium tetrahydroborate; In methanol; at 0 - 20 ℃; for 17h;

DOI:10.1002/ejoc.201200974

Reference yield: 48.0%

benzyl (2S,5R)-5-allyl-2-formylpyrrolidine-1-carboxylate (1437682-37-5) + di-n-propyl zinc (628-91-1) → benzyl (2S,2αS,5R)-(-)-5-allyl-2-(1-hydroxybutyl)pyrrolidine-1-carboxylate (1437682-39-7)

Guidance literature:

In tetrahydrofuran; at -78 - 20 ℃; for 3h;

DOI:10.1002/ejoc.201200974

upstream raw materials:

benzyl (2S,5R)-(-)-5-allyl-2-(hydroxymethyl)pyrrolidine-1-carboxylate

(2S,5R)-5-allylpyrrolidine-1,2-dicarboxylic acid 1-benzylester 2-methylester

benzyl (2S,5R)-5-allyl-2-formylpyrrolidine-1-carboxylate

n-propylmagnesium bromide

Downstream raw materials:

benzyl (2S,2αS,5R)-(+)-2-(1-hydroxybutyl)-5-[(E)-4-oxohept-2-enyl]pyrrolidine-1-carboxylate

benzyl (2S,2αS,5R)-2-(1-hydroxybutyl)-5-[(E)-4-oxoundec-2-enyl]-pyrrolidine-1-carboxylate