(3R,4S)-benzyl-1-(but-2-enylsulfonyl)-4-((R)-1-phenylethylamino)pyrrolidine-3-carboxylate

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Chemical Name:(3R,4S)-benzyl-1-(but-2-enylsulfonyl)-4-((R)-1-phenylethylamino)pyrrolidine-3-carboxylate
CAS No.:911286-93-6
Molecular Formula:C₂₄H₃₀N₂O₄S
Molecular Weight:442.579
Hs Code.:

Synonyms:(3R,4S)-benzyl-1-(but-2-enylsulfonyl)-4-((R)-1-phenylethylamino)pyrrolidine-3-carboxylate

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Chemical Property of (3R,4S)-benzyl-1-(but-2-enylsulfonyl)-4-((R)-1-phenylethylamino)pyrrolidine-3-carboxylate

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Technology Process of (3R,4S)-benzyl-1-(but-2-enylsulfonyl)-4-((R)-1-phenylethylamino)pyrrolidine-3-carboxylate

There total 3 articles about (3R,4S)-benzyl-1-(but-2-enylsulfonyl)-4-((R)-1-phenylethylamino)pyrrolidine-3-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: 79.0%

: prop-2-ene-1-sulfonyl chloride

: 911286-89-0
(3R,4S)-benzyl 1-tert-butyl 4-((R)-1-phenylethylamino)pyrrolidine-1,3-dicarboxylate

: 911286-93-6
(3R,4S)-benzyl-1-(but-2-enylsulfonyl)-4-((R)-1-phenylethylamino)pyrrolidine-3-carboxylate

Guidance literature:: (3R,4S)-benzyl 1-tert-butyl 4-((R)-1-phenylethylamino)pyrrolidine-1,3-dicarboxylate; With trifluoroacetic acid; In dichloromethane; at 0 ℃; for 1.5h;

prop-2-ene-1-sulfonyl chloride; With N-ethyl-N,N-diisopropylamine; In dichloromethane;
DOI:10.1021/ja0614565

Reference yield:

: 146256-98-6
4-oxo-pyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester

: 911286-93-6
(3R,4S)-benzyl-1-(but-2-enylsulfonyl)-4-((R)-1-phenylethylamino)pyrrolidine-3-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1.1: AcOH / ethanol / 4 h / 20 °C

1.2: NaCNBH₃ / ethanol / 16 h / 75 °C

1.3: 25 percent / HCl / ethyl acetate; dioxane / 3 h / 0 °C

2.1: LiOH*H₂O / tetrahydrofuran; methanol; H₂O / 2 h / 0 °C

2.2: HCl / tetrahydrofuran; methanol; H₂O / pH 5

2.3: 86 percent / Cs₂CO₃ / dimethylformamide / 3 h / 20 °C

3.1: TFA / CH₂Cl₂ / 1.5 h / 0 °C

3.2: 79 percent / N,N-di-iso-propylethylamine / CH₂Cl₂

With lithium hydroxide; acetic acid; trifluoroacetic acid; In tetrahydrofuran; methanol; ethanol; dichloromethane; water;
DOI:10.1021/ja0614565

Reference yield:

: 346610-81-9,267230-41-1
(3S,4R)-1-(N-tert-butoxycarbonyl)-3-[(1'R)-phenylethylamino]pyrrolidine-4-carboxylic acid ethyl ester hydrochloride

: 911286-93-6
(3R,4S)-benzyl-1-(but-2-enylsulfonyl)-4-((R)-1-phenylethylamino)pyrrolidine-3-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1.1: LiOH*H₂O / tetrahydrofuran; methanol; H₂O / 2 h / 0 °C

1.2: HCl / tetrahydrofuran; methanol; H₂O / pH 5

1.3: 86 percent / Cs₂CO₃ / dimethylformamide / 3 h / 20 °C

2.1: TFA / CH₂Cl₂ / 1.5 h / 0 °C

2.2: 79 percent / N,N-di-iso-propylethylamine / CH₂Cl₂

With lithium hydroxide; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; water;
DOI:10.1021/ja0614565