(3R,4S)-benzyl 1-tert-butyl 4-((R)-1-phenylethylamino)pyrrolidine-1,3-dicarboxylate

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Chemical Name:(3R,4S)-benzyl 1-tert-butyl 4-((R)-1-phenylethylamino)pyrrolidine-1,3-dicarboxylate
CAS No.:911286-89-0
Molecular Formula:C₂₅H₃₂N₂O₄
Molecular Weight:424.54
Hs Code.:

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

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Chemical Property of (3R,4S)-benzyl 1-tert-butyl 4-((R)-1-phenylethylamino)pyrrolidine-1,3-dicarboxylate

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Technology Process of (3R,4S)-benzyl 1-tert-butyl 4-((R)-1-phenylethylamino)pyrrolidine-1,3-dicarboxylate

There total 4 articles about (3R,4S)-benzyl 1-tert-butyl 4-((R)-1-phenylethylamino)pyrrolidine-1,3-dicarboxylate 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: 86.0%

: 100-39-0
benzyl bromide

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

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

Guidance literature:: (3S,4R)-1-(N-tert-butoxycarbonyl)-3-[(1'R)-phenylethylamino]pyrrolidine-4-carboxylic acid ethyl ester hydrochloride; With lithium hydroxide; In tetrahydrofuran; methanol; water; at 0 ℃; for 2h;

With hydrogenchloride; In tetrahydrofuran; methanol; water; pH=5;

benzyl bromide; With caesium carbonate; In N,N-dimethyl-formamide; at 20 ℃; for 3h;
DOI:10.1021/ja0614565

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 4 steps

1.1: 99 percent / NaHCO₃ / acetonitrile / 16 h / 20 °C

2.1: NaH / toluene / 1 h / 20 °C

2.2: 62 percent / toluene / 4.5 h / 0 °C

3.1: AcOH / ethanol / 4 h / 20 °C

3.2: NaCNBH₃ / ethanol / 16 h / 75 °C

3.3: 25 percent / HCl / ethyl acetate; dioxane / 3 h / 0 °C

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

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

4.3: 86 percent / Cs₂CO₃ / dimethylformamide / 3 h / 20 °C

With lithium hydroxide; sodium hydride; sodium hydrogencarbonate; acetic acid; In tetrahydrofuran; methanol; ethanol; water; toluene; acetonitrile;
DOI:10.1021/ja0614565

Reference yield:

: 14719-37-0
ethyl 2-(tert-butoxycarbonylamino)acetate

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

Guidance literature:: Multi-step reaction with 3 steps

1.1: NaH / toluene / 1 h / 20 °C

1.2: 62 percent / toluene / 4.5 h / 0 °C

2.1: AcOH / ethanol / 4 h / 20 °C

2.2: NaCNBH₃ / ethanol / 16 h / 75 °C

2.3: 25 percent / HCl / ethyl acetate; dioxane / 3 h / 0 °C

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

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

3.3: 86 percent / Cs₂CO₃ / dimethylformamide / 3 h / 20 °C

With lithium hydroxide; sodium hydride; acetic acid; In tetrahydrofuran; methanol; ethanol; water; toluene;
DOI:10.1021/ja0614565