(S)-4-[1-(4-Ethoxy-phenyl)-meth-(E)-ylidene]-2-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester

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Chemical Name:(S)-4-[1-(4-Ethoxy-phenyl)-meth-(E)-ylidene]-2-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester
CAS No.:540501-39-1
Molecular Formula:C₁₉H₂₇NO₄
Molecular Weight:333.428
Hs Code.:

Synonyms:(S)-4-[1-(4-Ethoxy-phenyl)-meth-(E)-ylidene]-2-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester

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Chemical Property of (S)-4-[1-(4-Ethoxy-phenyl)-meth-(E)-ylidene]-2-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester

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Technology Process of (S)-4-[1-(4-Ethoxy-phenyl)-meth-(E)-ylidene]-2-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester

There total 8 articles about (S)-4-[1-(4-Ethoxy-phenyl)-meth-(E)-ylidene]-2-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl 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: 77.0%

: 540501-28-8
(S)-2-tert-butyldimethylsilyloxymethyl-N-tert-butyloxycarbonyl-4-(4'-ethoxyphenyl)methylenepyrrolidine

: 540501-39-1
(S)-4-[1-(4-Ethoxy-phenyl)-meth-(E)-ylidene]-2-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 6h;
DOI:10.1021/jo034214l

Reference yield:

: 24424-99-5
di-tert-butyl dicarbonate

: 540501-39-1
(S)-4-[1-(4-Ethoxy-phenyl)-meth-(E)-ylidene]-2-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: aqueous Na₂CO₃ / tetrahydrofuran; dioxane / 18 h

2.1: NMM / 1,2-dimethoxy-ethane / 0.5 h / -20 °C

3.1: 11.96 g / NaBH₄ / 1,2-dimethoxy-ethane; H₂O / 0.33 h / Cooling

4.1: 78 percent / TEA; DMAP / CH₂Cl₂

5.1: 88 percent / trichloroisocyanuric acid; TEMPO / CH₂Cl₂ / 1 h / 0 °C

6.1: potassium tert-butoxide / tetrahydrofuran / 1 h / 20 °C

6.2: 69 percent / tetrahydrofuran / 20 °C

7.1: 77 percent / TBAF / tetrahydrofuran / 6 h / 20 °C

With 4-methyl-morpholine; dmap; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium tetrahydroborate; TEA; trichloroisocyanuric acid; potassium tert-butylate; tetrabutyl ammonium fluoride; sodium carbonate; In tetrahydrofuran; 1,4-dioxane; 1,2-dimethoxyethane; dichloromethane; water; 6.2: Wittig reaction;
DOI:10.1021/jo034214l

Reference yield:

: 61478-26-0
tert-butyl (2S,4R)-4-hydroxy-2-hydroxymethyl-pyrrolidine-1-carboxylate

: 540501-39-1
(S)-4-[1-(4-Ethoxy-phenyl)-meth-(E)-ylidene]-2-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: 78 percent / TEA; DMAP / CH₂Cl₂

2.1: 88 percent / trichloroisocyanuric acid; TEMPO / CH₂Cl₂ / 1 h / 0 °C

3.1: potassium tert-butoxide / tetrahydrofuran / 1 h / 20 °C

3.2: 69 percent / tetrahydrofuran / 20 °C

4.1: 77 percent / TBAF / tetrahydrofuran / 6 h / 20 °C

With dmap; 2,2,6,6-tetramethyl-piperidine-N-oxyl; TEA; trichloroisocyanuric acid; potassium tert-butylate; tetrabutyl ammonium fluoride; In tetrahydrofuran; dichloromethane; 3.2: Wittig reaction;
DOI:10.1021/jo034214l