(E)-3-[(2R,3S)-1-Acetyl-3-(acetyl-benzyl-amino)-pyrrolidin-2-yl]-acrylic acid methyl ester

Base Information

• Chemical Name: (E)-3-[(2R,3S)-1-Acetyl-3-(acetyl-benzyl-amino)-pyrrolidin-2-yl]-acrylic acid methyl ester
• CAS No.: 203982-62-1
• Molecular Formula: C₁₉H₂₄N₂O₄
• Molecular Weight: 344.411

Synonyms:(E)-3-[(2R,3S)-1-Acetyl-3-(acetyl-benzyl-amino)-pyrrolidin-2-yl]-acrylic acid methyl ester

Chemical Property of (E)-3-[(2R,3S)-1-Acetyl-3-(acetyl-benzyl-amino)-pyrrolidin-2-yl]-acrylic acid methyl ester

Chemical Property:

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Technology Process of (E)-3-[(2R,3S)-1-Acetyl-3-(acetyl-benzyl-amino)-pyrrolidin-2-yl]-acrylic acid methyl ester

There total 5 articles about (E)-3-[(2R,3S)-1-Acetyl-3-(acetyl-benzyl-amino)-pyrrolidin-2-yl]-acrylic acid methyl 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: 79.0%

methyl (triphenylphosphoranylidene)acetate (21204-67-1,2605-67-6) + N-((2S,3S)-1-Acetyl-2-formyl-pyrrolidin-3-yl)-N-benzyl-acetamide (203982-61-0) → (E)-3-[(2R,3S)-1-Acetyl-3-(acetyl-benzyl-amino)-pyrrolidin-2-yl]-acrylic acid methyl ester (203982-62-1)

Guidance literature:

In tetrahydrofuran;

DOI:10.1016/S0040-4039(97)10749-3

Reference yield:

(4S,5S)-4-N-benzylamino-5-hydroxymethylpyrrolidin-2-one (203982-57-4) → (E)-3-[(2R,3S)-1-Acetyl-3-(acetyl-benzyl-amino)-pyrrolidin-2-yl]-acrylic acid methyl ester (203982-62-1)

Guidance literature:

Multi-step reaction with 4 steps

1: LiAlH₄ / tetrahydrofuran

2: pyridine

3: 82 percent / SO₃, pyridine / dimethylsulfoxide / Ambient temperature

4: 79 percent / tetrahydrofuran

With pyridine; lithium aluminium tetrahydride; sulfur trioxide; In tetrahydrofuran; dimethyl sulfoxide;

DOI:10.1016/S0040-4039(97)10749-3

Reference yield:

(2R,5R,6S)-6-N-benzylamino-2-phenyl-3-oxa-1-azabicyclo[3.3.0]octane-8-one (199436-23-2) → (E)-3-[(2R,3S)-1-Acetyl-3-(acetyl-benzyl-amino)-pyrrolidin-2-yl]-acrylic acid methyl ester (203982-62-1)

Guidance literature:

Multi-step reaction with 5 steps

1: CF₃COOH / tetrahydrofuran; H₂O

2: LiAlH₄ / tetrahydrofuran

3: pyridine

4: 82 percent / SO₃, pyridine / dimethylsulfoxide / Ambient temperature

5: 79 percent / tetrahydrofuran

With pyridine; lithium aluminium tetrahydride; sulfur trioxide; trifluoroacetic acid; In tetrahydrofuran; water; dimethyl sulfoxide;

DOI:10.1016/S0040-4039(97)10749-3

upstream raw materials:

methyl (triphenylphosphoranylidene)acetate

N-((2S,3S)-1-Acetyl-2-formyl-pyrrolidin-3-yl)-N-benzyl-acetamide

((2S,3S)-3-Benzylamino-pyrrolidin-2-yl)-methanol

N-((2S,3S)-1-Acetyl-2-hydroxymethyl-pyrrolidin-3-yl)-N-benzyl-acetamide

Downstream raw materials:

3-[(2R,3S)-1-Acetyl-3-(acetyl-benzyl-amino)-pyrrolidin-2-yl]-propionic acid methyl ester

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