(3S,4R,5R)-[5-(tertbutyldimethylsilanyloxymethyl)-4-(1H-indol-3-yl)-2-oxopyrrolidin-3-yl]carbamic acid benzyl ester

Base Information

Chemical Name:(3S,4R,5R)-[5-(tertbutyldimethylsilanyloxymethyl)-4-(1H-indol-3-yl)-2-oxopyrrolidin-3-yl]carbamic acid benzyl ester
CAS No.:505086-85-1
Molecular Formula:C₂₇H₃₅N₃O₄Si
Molecular Weight:493.678
Hs Code.:

Synonyms:(3S,4R,5R)-[5-(tertbutyldimethylsilanyloxymethyl)-4-(1H-indol-3-yl)-2-oxopyrrolidin-3-yl]carbamic acid benzyl ester

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Chemical Property of (3S,4R,5R)-[5-(tertbutyldimethylsilanyloxymethyl)-4-(1H-indol-3-yl)-2-oxopyrrolidin-3-yl]carbamic acid benzyl ester

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Technology Process of (3S,4R,5R)-[5-(tertbutyldimethylsilanyloxymethyl)-4-(1H-indol-3-yl)-2-oxopyrrolidin-3-yl]carbamic acid benzyl ester

There total 11 articles about (3S,4R,5R)-[5-(tertbutyldimethylsilanyloxymethyl)-4-(1H-indol-3-yl)-2-oxopyrrolidin-3-yl]carbamic acid benzyl 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: 80.0%

: 100-51-6,185532-71-2
benzyl alcohol

: 505086-84-0
5-(tert-butyl-dimethyl-silanyloxymethyl)-4-(1H-indol-3-yl)-2-oxo-pyrrolidine-3-carboxylic acid

: 505086-85-1
(3S,4R,5R)-[5-(tertbutyldimethylsilanyloxymethyl)-4-(1H-indol-3-yl)-2-oxopyrrolidin-3-yl]carbamic acid benzyl ester

Guidance literature:: 5-(tert-butyl-dimethyl-silanyloxymethyl)-4-(1H-indol-3-yl)-2-oxo-pyrrolidine-3-carboxylic acid; With diphenyl-phosphinic acid; triethylamine; In acetonitrile; at 0 - 20 ℃; for 2.5h;

In tetrahydrofuran; for 1h; Heating;

benzyl alcohol; In tetrahydrofuran; for 24h; Heating;
DOI:10.1016/j.tetasy.2005.02.008

Reference yield:

: 505086-79-3
(R,R)-4-[(2,2-dimethyl-4,6-dioxo[1,3]dioxan-5-yl)(1H-indol-3-yl)methyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylic acid benzyl ester

: 505086-85-1
(3S,4R,5R)-[5-(tertbutyldimethylsilanyloxymethyl)-4-(1H-indol-3-yl)-2-oxopyrrolidin-3-yl]carbamic acid benzyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: AcOH; H₂ / Pd/C / ethanol / 20 h / 20 °C

1.2: 63 percent / methanol; diethyl ether / 0.5 h / 0 °C

2.1: 80 percent / imidazole / dimethylformamide

3.1: 87 percent / aq. KOH / tetrahydrofuran / 20 °C

4.1: DPPA; Et₃N / acetonitrile / 2.5 h / 0 - 20 °C

4.2: tetrahydrofuran / 1 h / Heating

4.3: 80 percent / tetrahydrofuran / 24 h / Heating

With 1H-imidazole; potassium hydroxide; diphenyl-phosphinic acid; hydrogen; acetic acid; triethylamine; palladium on activated charcoal; In tetrahydrofuran; ethanol; N,N-dimethyl-formamide; acetonitrile; 4.2: Curtius rearrangement;
DOI:10.1016/j.tetasy.2005.02.008

Reference yield:

: 120-72-9
indole

: 505086-85-1
(3S,4R,5R)-[5-(tertbutyldimethylsilanyloxymethyl)-4-(1H-indol-3-yl)-2-oxopyrrolidin-3-yl]carbamic acid benzyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 90 percent / D,L-proline / acetonitrile

2: 73 percent / HCl / Heating

3: imidazole / CH₂Cl₂; dimethylformamide

4: KOH / tetrahydrofuran / 0 °C

5: diphenylphosphonyl azide; Et₃N

6: tetrahydrofuran / Heating

With 1H-imidazole; hydrogenchloride; potassium hydroxide; diphenyl phosphoryl azide; triethylamine; rac-Pro-OH; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 6: Curtius rearrangement;
DOI:10.1016/S0040-4039(02)02537-6