(2S)-N-(tert-butoxycarbonyl)-2-[(4'-benzyloxy-1'-oxo)-E-but-2'-enyl]pyrrolidine

Base Information

• Chemical Name: (2S)-N-(tert-butoxycarbonyl)-2-[(4'-benzyloxy-1'-oxo)-E-but-2'-enyl]pyrrolidine
• CAS No.: 617689-99-3
• Molecular Formula: C₂₀H₂₇NO₄
• Molecular Weight: 345.439
• Mol file: 617689-99-3.mol

Synonyms:(2S)-N-(tert-butoxycarbonyl)-2-[(4'-benzyloxy-1'-oxo)-E-but-2'-enyl]pyrrolidine

Chemical Property of (2S)-N-(tert-butoxycarbonyl)-2-[(4'-benzyloxy-1'-oxo)-E-but-2'-enyl]pyrrolidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S)-N-(tert-butoxycarbonyl)-2-[(4'-benzyloxy-1'-oxo)-E-but-2'-enyl]pyrrolidine

There total 2 articles about (2S)-N-(tert-butoxycarbonyl)-2-[(4'-benzyloxy-1'-oxo)-E-but-2'-enyl]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: 68.0%

benzyloxyacetoaldehyde (60656-87-3) + dimethyl 2-((S)-1-(tert-butoxycarbonyl)pyrrolidin-2-yl)-2-oxoethylphosphonate (617689-98-2) → (2S)-N-(tert-butoxycarbonyl)-2-[(4'-benzyloxy-1'-oxo)-E-but-2'-enyl]pyrrolidine (617689-99-3)

Guidance literature:

With potassium carbonate; In acetonitrile; at 20 ℃; for 48h;

DOI:10.1016/S0040-4020(03)00918-9

Reference yield:

(S)-N-(tert-butoxycarbonyl)proline methyl ester (59936-29-7) → (2S)-N-(tert-butoxycarbonyl)-2-[(4'-benzyloxy-1'-oxo)-E-but-2'-enyl]pyrrolidine (617689-99-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: n-BuLi / tetrahydrofuran / -65 - -20 °C

1.2: 85.2 percent / tetrahydrofuran / -78 - 20 °C

2.1: 68 percent / K₂CO₃ / acetonitrile / 48 h / 20 °C

With n-butyllithium; potassium carbonate; In tetrahydrofuran; acetonitrile;

DOI:10.1016/S0040-4020(03)00918-9

Reference yield: 63.6%

(2S)-N-(tert-butoxycarbonyl)-2-[(4'-benzyloxy-1'-oxo)-E-but-2'-enyl]pyrrolidine (617689-99-3) → (2S,1'R)-N-(tert-butoxycarbonyl)-2-[(4'-benzyloxy-1'-hydroxy)-E-but-2'-enyl]pyrrolidine (617690-00-3) + (2S,1'S)-N-(tert-butoxycarbonyl)-2-[(4'-benzyloxy-1'-hydroxy)-E-but-2'-enyl]pyrrolidine

Guidance literature:

With sodium tetrahydroborate; cerium(III) chloride; In methanol; at 20 ℃; for 0.166667h;

DOI:10.1016/S0040-4020(03)00918-9

upstream raw materials:

benzyloxyacetoaldehyde

dimethyl 2-((S)-1-(tert-butoxycarbonyl)pyrrolidin-2-yl)-2-oxoethylphosphonate

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

Downstream raw materials:

(2S,1'R)-N-(tert-butoxycarbonyl)-2-[(4'-benzyloxy-1'-hydroxy)-E-but-2'-enyl]pyrrolidine

(2S,1'S,2'S,3'S)-N-(tert-butoxycarbonyl)-2-[(4'-benzyloxy-1',2',3'-trihydroxy)butyl]pyrrolidine

(2S,1'S,2'S,3'S)-N-(tert-butoxycarbonyl)-2-[(1',2',3'-triacetoxy-4'-benzyloxy)butyl]pyrrolidine