(2S,5S)-N-(4-benzyloxybutyryl)-2,5-bis(methoxymethoxymethyl)pyrrolidine

Base Information

• Chemical Name: (2S,5S)-N-(4-benzyloxybutyryl)-2,5-bis(methoxymethoxymethyl)pyrrolidine
• CAS No.: 374590-18-8
• Molecular Formula: C₂₁H₃₃NO₆
• Molecular Weight: 395.496
• Mol file: 374590-18-8.mol

Synonyms:(2S,5S)-N-(4-benzyloxybutyryl)-2,5-bis(methoxymethoxymethyl)pyrrolidine

Chemical Property of (2S,5S)-N-(4-benzyloxybutyryl)-2,5-bis(methoxymethoxymethyl)pyrrolidine

Chemical Property:

Purity/Quality:

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Technology Process of (2S,5S)-N-(4-benzyloxybutyryl)-2,5-bis(methoxymethoxymethyl)pyrrolidine

There total 1 articles about (2S,5S)-N-(4-benzyloxybutyryl)-2,5-bis(methoxymethoxymethyl)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: 81.0%

4-(benzyloxy)butanoic acid (10385-30-5) + (2S,5S)-bis(methoxymethoxymethyl)pyrrolidine (93621-95-5) → (2S,5S)-N-(4-benzyloxybutyryl)-2,5-bis(methoxymethoxymethyl)pyrrolidine (374590-18-8)

Guidance literature:

With dicyclohexyl-carbodiimide; In dichloromethane; at 0 ℃; for 12h;

DOI:10.1016/S0040-4039(01)01260-6

Reference yield: 2.0%

(S)-2-phenylpent-4-enoyl chloride (374590-17-7) + (2S,5S)-N-(4-benzyloxybutyryl)-2,5-bis(methoxymethoxymethyl)pyrrolidine (374590-18-8) → (2R,4S)-2-(2-Benzyloxy-ethyl)-1-((2S,5S)-2,5-bis-methoxymethoxymethyl-pyrrolidin-1-yl)-4-phenyl-hept-6-ene-1,3-dione + (2S,4S)-2-(2-Benzyloxy-ethyl)-1-((2S,5S)-2,5-bis-methoxymethoxymethyl-pyrrolidin-1-yl)-4-phenyl-hept-6-ene-1,3-dione (374590-19-9)

Guidance literature:

With lithium diisopropyl amide; at -78 ℃; for 0.0833333h;

DOI:10.1016/S0040-4039(01)01260-6

Reference yield:

(2S,5S)-N-(4-benzyloxybutyryl)-2,5-bis(methoxymethoxymethyl)pyrrolidine (374590-18-8) → (2S,3R,4S)-2-(2-Benzyloxy-ethyl)-1-((2S,5S)-2,5-bis-methoxymethoxymethyl-pyrrolidin-1-yl)-3-hydroxy-4-phenyl-hept-6-en-1-one

Guidance literature:

Multi-step reaction with 2 steps

1: LDA / 0.08 h / -78 °C

2: Zn(BH₄)2

With zinc(II) tetrahydroborate; lithium diisopropyl amide;

DOI:10.1016/S0040-4039(01)01260-6

upstream raw materials:

4-(benzyloxy)butanoic acid

(2S,5S)-bis(methoxymethoxymethyl)pyrrolidine

Downstream raw materials:

(2S,4S)-2-(2-Benzyloxy-ethyl)-1-((2S,5S)-2,5-bis-methoxymethoxymethyl-pyrrolidin-1-yl)-4-phenyl-hept-6-ene-1,3-dione