(2S,5R)-5-Allyl-1-(2-benzyloxy-3-phenyl-pent-4-enoyl)-pyrrolidine-2-carboxylic acid methyl ester

Base Information

• Chemical Name: (2S,5R)-5-Allyl-1-(2-benzyloxy-3-phenyl-pent-4-enoyl)-pyrrolidine-2-carboxylic acid methyl ester
• CAS No.: 210345-12-3
• Molecular Formula: C₂₇H₃₁NO₄
• Molecular Weight: 433.547
• Mol file: 210345-12-3.mol

Synonyms:(2S,5R)-5-Allyl-1-(2-benzyloxy-3-phenyl-pent-4-enoyl)-pyrrolidine-2-carboxylic acid methyl ester

Chemical Property of (2S,5R)-5-Allyl-1-(2-benzyloxy-3-phenyl-pent-4-enoyl)-pyrrolidine-2-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

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MSDS Files:

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Technology Process of (2S,5R)-5-Allyl-1-(2-benzyloxy-3-phenyl-pent-4-enoyl)-pyrrolidine-2-carboxylic acid methyl ester

There total 2 articles about (2S,5R)-5-Allyl-1-(2-benzyloxy-3-phenyl-pent-4-enoyl)-pyrrolidine-2-carboxylic acid methyl 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: 65.0%

2-benzyloxy-3-phenyl-4-pentenoic acid + (5R,2S)-5-allyl-pyrrolidine-2-carboxylic acid methyl ester (210345-08-7) → (2S,5R)-5-Allyl-1-(2-benzyloxy-3-phenyl-pent-4-enoyl)-pyrrolidine-2-carboxylic acid methyl ester (210345-12-3)

Guidance literature:

With N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; In dichloromethane; 0 deg C to RT;

DOI:10.1016/S0040-4039(98)00858-2

Reference yield:

(S)-N-(tert-butoxycarbonyl)proline methyl ester (59936-29-7) → (2S,5R)-5-Allyl-1-(2-benzyloxy-3-phenyl-pent-4-enoyl)-pyrrolidine-2-carboxylic acid methyl ester (210345-12-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) MeOH, Et₄NOTs; 2.) TiCl₄ / 1.) carbon anode, Pt cathode, 3.0 F/mol, 26.8 mA; 2.) CH₂Cl₂, -78 deg C to RT

2: 65 percent / EDC, Et₃N / CH₂Cl₂ / 0 deg C to RT

With methanol; titanium tetrachloride; tetraethylammonium tosylate; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; In dichloromethane;

DOI:10.1016/S0040-4039(98)00858-2

Reference yield: 72.0%

(2S,5R)-5-Allyl-1-(2-benzyloxy-3-phenyl-pent-4-enoyl)-pyrrolidine-2-carboxylic acid methyl ester (210345-12-3) → (Z)-(3S,10aR)-6-Benzyloxy-5-oxo-7-phenyl-1,2,3,5,6,7,10,10a-octahydro-pyrrolo[1,2-a]azocine-3-carboxylic acid methyl ester

Guidance literature:

With Grubbs catalyst first generation; In dichloromethane; at 40 ℃;

DOI:10.1016/S0040-4039(98)00858-2

upstream raw materials:

(5R,2S)-5-allyl-pyrrolidine-2-carboxylic acid methyl ester

(S)-N-(tert-butoxycarbonyl)proline methyl ester