(E)-3-(1-Benzyloxymethyl-5-oxo-4,5,6,7-tetrahydro-1H-pyrrolo[2,3-c]pyridin-3-yl)-acrylic acid ethyl ester

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Chemical Name:(E)-3-(1-Benzyloxymethyl-5-oxo-4,5,6,7-tetrahydro-1H-pyrrolo[2,3-c]pyridin-3-yl)-acrylic acid ethyl ester
CAS No.:191936-86-4
Molecular Formula:C₂₀H₂₂N₂O₄
Molecular Weight:354.406
Hs Code.:

Synonyms:(E)-3-(1-Benzyloxymethyl-5-oxo-4,5,6,7-tetrahydro-1H-pyrrolo[2,3-c]pyridin-3-yl)-acrylic acid ethyl ester

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Chemical Property of (E)-3-(1-Benzyloxymethyl-5-oxo-4,5,6,7-tetrahydro-1H-pyrrolo[2,3-c]pyridin-3-yl)-acrylic acid ethyl ester

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Technology Process of (E)-3-(1-Benzyloxymethyl-5-oxo-4,5,6,7-tetrahydro-1H-pyrrolo[2,3-c]pyridin-3-yl)-acrylic acid ethyl ester

There total 6 articles about (E)-3-(1-Benzyloxymethyl-5-oxo-4,5,6,7-tetrahydro-1H-pyrrolo[2,3-c]pyridin-3-yl)-acrylic acid ethyl 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: 92.0%

: 1071-46-1
hydrogen ethyl malonate

: 191936-85-3
1-Benzyloxymethyl-5-oxo-4,5,6,7-tetrahydro-1H-pyrrolo[2,3-c]pyridine-3-carbaldehyde

: 191936-86-4
(E)-3-(1-Benzyloxymethyl-5-oxo-4,5,6,7-tetrahydro-1H-pyrrolo[2,3-c]pyridin-3-yl)-acrylic acid ethyl ester

Guidance literature:: With piperidine; In pyridine; 1) 80 deg C, 16 h, 2) reflux, 6 h;
DOI:10.1016/S0040-4020(97)00469-9

Reference yield:

: 184921-36-6
4-Ethoxycarbonylmethyl-5-(hydroxyimino-methyl)-1H-pyrrole-3-carboxylic acid ethyl ester

: 191936-86-4
(E)-3-(1-Benzyloxymethyl-5-oxo-4,5,6,7-tetrahydro-1H-pyrrolo[2,3-c]pyridin-3-yl)-acrylic acid ethyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: H₂, 2 N HCl / Pd(OH)2-C / ethanol / 2 h / Ambient temperature

2: 474 mg / NaOEt / ethanol / 5 h / 40 °C

3: 1) NaH / 1) DMF, room temperature, 40 min, 2) DMF, 5 h

4: 65 percent / DIBAL / toluene; CH₂Cl₂ / 0.5 h

5: 70 percent / Dess Martin periodinane / CH₂Cl₂ / 1 h / Ambient temperature

6: 92 percent / piperidine / pyridine / 1) 80 deg C, 16 h, 2) reflux, 6 h

With piperidine; hydrogenchloride; hydrogen; sodium ethanolate; sodium hydride; diisobutylaluminium hydride; Dess-Martin periodane; palladium hydroxide - carbon; In pyridine; ethanol; dichloromethane; toluene;
DOI:10.1016/S0040-4020(97)00469-9

Reference yield:

: 184921-37-7
5-Aminomethyl-4-ethoxycarbonylmethyl-1H-pyrrole-3-carboxylic acid ethyl ester

: 191936-86-4
(E)-3-(1-Benzyloxymethyl-5-oxo-4,5,6,7-tetrahydro-1H-pyrrolo[2,3-c]pyridin-3-yl)-acrylic acid ethyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 474 mg / NaOEt / ethanol / 5 h / 40 °C

2: 1) NaH / 1) DMF, room temperature, 40 min, 2) DMF, 5 h

3: 65 percent / DIBAL / toluene; CH₂Cl₂ / 0.5 h

4: 70 percent / Dess Martin periodinane / CH₂Cl₂ / 1 h / Ambient temperature

5: 92 percent / piperidine / pyridine / 1) 80 deg C, 16 h, 2) reflux, 6 h

With piperidine; sodium ethanolate; sodium hydride; diisobutylaluminium hydride; Dess-Martin periodane; In pyridine; ethanol; dichloromethane; toluene;
DOI:10.1016/S0040-4020(97)00469-9