(S,E)-methyl 4-ethylidene-1-(4-hydroxy-3-methoxybenzoyl)pyrrolidine-2-carboxylate

Base Information

Chemical Name:(S,E)-methyl 4-ethylidene-1-(4-hydroxy-3-methoxybenzoyl)pyrrolidine-2-carboxylate
CAS No.:1450821-35-8
Molecular Formula:C₁₆H₁₉NO₅
Molecular Weight:305.331
Hs Code.:

Synonyms:(S,E)-methyl 4-ethylidene-1-(4-hydroxy-3-methoxybenzoyl)pyrrolidine-2-carboxylate

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Chemical Property of (S,E)-methyl 4-ethylidene-1-(4-hydroxy-3-methoxybenzoyl)pyrrolidine-2-carboxylate

Chemical Property:

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Technology Process of (S,E)-methyl 4-ethylidene-1-(4-hydroxy-3-methoxybenzoyl)pyrrolidine-2-carboxylate

There total 8 articles about (S,E)-methyl 4-ethylidene-1-(4-hydroxy-3-methoxybenzoyl)pyrrolidine-2-carboxylate 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:

: 121-34-6
3-methoxy-4-hydroxybenzoic acid

: 1450821-34-7
(S,E)-methyl 4-ethylidenepyrrolidine-2-carboxylate hydrochloride

: 1450821-35-8
(S,E)-methyl 4-ethylidene-1-(4-hydroxy-3-methoxybenzoyl)pyrrolidine-2-carboxylate

Guidance literature:: 3-methoxy-4-hydroxybenzoic acid; With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 20 ℃; for 0.5h;

(S,E)-methyl 4-ethylidenepyrrolidine-2-carboxylate hydrochloride; In tetrahydrofuran; for 16h;
DOI:10.1021/ol4019453

Reference yield:

: 1450821-30-3
(S)-2-((3-hydroxy-2-methylenebutyl)(4-methoxybenzyl)amino)acetic acid 2,2,2-trifluoroacetic acid salt

: 1450821-35-8
(S,E)-methyl 4-ethylidene-1-(4-hydroxy-3-methoxybenzoyl)pyrrolidine-2-carboxylate

Guidance literature:: Multi-step reaction with 5 steps

1.1: N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 15 h

2.1: N-ethyl-N,N-diisopropylamine; di-n-butylboryl trifluoromethanesulfonate / dichloromethane / 1.25 h / -78 - 10 °C

3.1: benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / dichloromethane / 16 h

4.1: carbonochloridic acid 1-chloro-ethyl ester / dichloromethane / 0.33 h / 0 °C

4.2: 0.67 h / Reflux

5.1: N-ethyl-N,N-diisopropylamine; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate / tetrahydrofuran / 0.5 h / 20 °C

5.2: 16 h

With carbonochloridic acid 1-chloro-ethyl ester; di-n-butylboryl trifluoromethanesulfonate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; 2.1: |Claisen-Ireland Rearrangement;
DOI:10.1021/ol4019453

Reference yield:

: 736158-13-7
(2S)-3-(bromomethyl)but-3-en-2-ol

: 1450821-35-8
(S,E)-methyl 4-ethylidene-1-(4-hydroxy-3-methoxybenzoyl)pyrrolidine-2-carboxylate

Guidance literature:: Multi-step reaction with 7 steps

1.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 16 h

2.1: dichloromethane / 4 h

3.1: N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 15 h

4.1: N-ethyl-N,N-diisopropylamine; di-n-butylboryl trifluoromethanesulfonate / dichloromethane / 1.25 h / -78 - 10 °C

5.1: benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / dichloromethane / 16 h

6.1: carbonochloridic acid 1-chloro-ethyl ester / dichloromethane / 0.33 h / 0 °C

6.2: 0.67 h / Reflux

7.1: N-ethyl-N,N-diisopropylamine; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate / tetrahydrofuran / 0.5 h / 20 °C

7.2: 16 h

With carbonochloridic acid 1-chloro-ethyl ester; di-n-butylboryl trifluoromethanesulfonate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; 4.1: |Claisen-Ireland Rearrangement;
DOI:10.1021/ol4019453