(2S^*,3S^*,4R^*)-3-<2-Hydroxyethyl>-4-isopropenyl-2-(methoxycarbonyl)-1-(phenoxyacetyl)pyrrolidine

Base Information

• Chemical Name: (2S^*,3S^*,4R^*)-3-<2-Hydroxyethyl>-4-isopropenyl-2-(methoxycarbonyl)-1-(phenoxyacetyl)pyrrolidine
• CAS No.: 137056-95-2
• Molecular Formula: C₁₉H₂₅NO₅
• Molecular Weight: 347.411

Synonyms:(2S^*,3S^*,4R^*)-3-<2-Hydroxyethyl>-4-isopropenyl-2-(methoxycarbonyl)-1-(phenoxyacetyl)pyrrolidine

Chemical Property of (2S^*,3S^*,4R^*)-3-<2-Hydroxyethyl>-4-isopropenyl-2-(methoxycarbonyl)-1-(phenoxyacetyl)pyrrolidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S^*,3S^*,4R^*)-3-<2-Hydroxyethyl>-4-isopropenyl-2-(methoxycarbonyl)-1-(phenoxyacetyl)pyrrolidine

There total 7 articles about (2S^*,3S^*,4R^*)-3-<2-Hydroxyethyl>-4-isopropenyl-2-(methoxycarbonyl)-1-(phenoxyacetyl)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: 84.0%

(2S*,3S*,4R*)-3-<2-(tert-Butyldimethylsiloxy)ethyl>-4-isopropenyl-2-(methoxycarbonyl)-1-(phenoxyacetyl)pyrrolidine (137007-50-2) → (2S*,3S*,4R*)-3-<2-Hydroxyethyl>-4-isopropenyl-2-(methoxycarbonyl)-1-(phenoxyacetyl)pyrrolidine (137056-95-2)

Guidance literature:

With acetic acid; In tetrahydrofuran; water; for 10h; Ambient temperature;

DOI:10.1021/jo00026a035

Reference yield:

phenoxyacetic anhydride (14316-61-1) → (2S*,3S*,4R*)-3-<2-Hydroxyethyl>-4-isopropenyl-2-(methoxycarbonyl)-1-(phenoxyacetyl)pyrrolidine (137056-95-2)

Guidance literature:

Multi-step reaction with 4 steps

1: Et₃N / CH₂Cl₂ / 4 h / Ambient temperature

2: 90 percent / H₂ / 5percent Pd/CaCO₃ / ethyl acetate / Ambient temperature

3: 1. n-BuLi / 1. hexane, Et₂O, 15 min, 0 deg C; 2. Et₂O, 14 h

4: 84 percent / AcOH / tetrahydrofuran; H₂O / 10 h / Ambient temperature

With n-butyllithium; hydrogen; acetic acid; triethylamine; Lindlar's catalyst; In tetrahydrofuran; dichloromethane; water; ethyl acetate;

DOI:10.1021/jo00026a035

Reference yield:

(E)-6-((tert-butyldimethylsilyl)oxy)hex-3-en-2-one (96429-43-5) → (2S*,3S*,4R*)-3-<2-Hydroxyethyl>-4-isopropenyl-2-(methoxycarbonyl)-1-(phenoxyacetyl)pyrrolidine (137056-95-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 92 percent / TBAF / tetrahydrofuran / 1 h / -78 °C

2: 88 percent / MeOH / Zn(OAc)2 / dimethylsulfoxide / 55 °C

3: Et₃N / CH₂Cl₂ / 4 h / Ambient temperature

4: 90 percent / H₂ / 5percent Pd/CaCO₃ / ethyl acetate / Ambient temperature

5: 1. n-BuLi / 1. hexane, Et₂O, 15 min, 0 deg C; 2. Et₂O, 14 h

6: 84 percent / AcOH / tetrahydrofuran; H₂O / 10 h / Ambient temperature

With methanol; n-butyllithium; tetrabutyl ammonium fluoride; hydrogen; acetic acid; triethylamine; Lindlar's catalyst; zinc diacetate; In tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide; ethyl acetate;

DOI:10.1021/jo00026a035

upstream raw materials:

(2S^*,3S^*,4R^*)-3-<2-(tert-Butyldimethylsiloxy)ethyl>-4-isopropenyl-2-(methoxycarbonyl)-1-(phenoxyacetyl)pyrrolidine

phenoxyacetic anhydride

(E)-6-((tert-butyldimethylsilyl)oxy)hex-3-en-2-one

3-Acetyl-4-<2-(tert-butyldimethylsiloxy)ethyl>-5-(methylcarbonyl)-2-pyrroline

Downstream raw materials:

(2S^*,3S^*,4R^*)-3-(Carboxymethyl)-4-isopropenyl-2-(methoxycarbonyl)-1-(phenoxyacetyl)pyrrolidine

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