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

Base Information

• Chemical Name: (2S^*,3S^*,4R^*)-3-<2-(tert-Butyldimethylsiloxy)ethyl>-4-isopropenyl-2-(methoxycarbonyl)-1-(phenoxyacetyl)pyrrolidine
• CAS No.: 137007-50-2
• Molecular Formula: C₂₅H₃₉NO₅Si
• Molecular Weight: 461.674

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

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

Chemical Property:

Purity/Quality:

98% ^*data from raw suppliers

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

There total 6 articles about (2S^*,3S^*,4R^*)-3-<2-(tert-Butyldimethylsiloxy)ethyl>-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:

phenoxyacetic anhydride (14316-61-1) → (2S*,3S*,4R*)-3-<2-(tert-Butyldimethylsiloxy)ethyl>-4-isopropenyl-2-(methoxycarbonyl)-1-(phenoxyacetyl)pyrrolidine (137007-50-2)

Guidance literature:

Multi-step reaction with 3 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

With n-butyllithium; hydrogen; triethylamine; Lindlar's catalyst; In dichloromethane; 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-(tert-Butyldimethylsiloxy)ethyl>-4-isopropenyl-2-(methoxycarbonyl)-1-(phenoxyacetyl)pyrrolidine (137007-50-2)

Guidance literature:

Multi-step reaction with 5 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

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

DOI:10.1021/jo00026a035

Reference yield:

3-Acetyl-4-<2-(tert-butyldimethylsiloxy)ethyl>-5-(methylcarbonyl)-2-pyrroline (137007-45-5,137007-46-6) → (2S*,3S*,4R*)-3-<2-(tert-Butyldimethylsiloxy)ethyl>-4-isopropenyl-2-(methoxycarbonyl)-1-(phenoxyacetyl)pyrrolidine (137007-50-2)

Guidance literature:

Multi-step reaction with 3 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

With n-butyllithium; hydrogen; triethylamine; Lindlar's catalyst; In dichloromethane; ethyl acetate;

DOI:10.1021/jo00026a035

upstream raw materials:

Methyltriphenylphosphonium bromide

(2S^*,3S^*,4S^*)-4-Acetyl-3-<2-(tert-butyldimethylsiloxy)ethyl>-2-(methoxycarbonyl)-1-(phenoxyacetyl)pyrrolidine

phenoxyacetic anhydride

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

Downstream raw materials:

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

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

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