(3R,4R)-3-[(3-acetoxy-4-acetoxymethylpyrrolidin-1-yl)methyl]benzamide

Base Information

• Chemical Name: (3R,4R)-3-[(3-acetoxy-4-acetoxymethylpyrrolidin-1-yl)methyl]benzamide
• CAS No.: 705060-10-2
• Molecular Formula: C₁₇H₂₂N₂O₅
• Molecular Weight: 334.372
• Mol file: 705060-10-2.mol

Synonyms:(3R,4R)-3-[(3-acetoxy-4-acetoxymethylpyrrolidin-1-yl)methyl]benzamide

Chemical Property of (3R,4R)-3-[(3-acetoxy-4-acetoxymethylpyrrolidin-1-yl)methyl]benzamide

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of (3R,4R)-3-[(3-acetoxy-4-acetoxymethylpyrrolidin-1-yl)methyl]benzamide

There total 4 articles about (3R,4R)-3-[(3-acetoxy-4-acetoxymethylpyrrolidin-1-yl)methyl]benzamide 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%

3-carboxamidobenzaldehyde (126534-87-0) + (3R,4R)-3-acetoxy-4-acetoxymethylpyrrolidine hydrochloride → (3R,4R)-3-[(3-acetoxy-4-acetoxymethylpyrrolidin-1-yl)methyl]benzamide (705060-10-2)

Guidance literature:

With sodium tris(acetoxy)borohydride; In 1,2-dichloro-ethane; at 20 ℃;

DOI:10.1021/ja038159+

Reference yield:

3-Cyanobenzaldehyde (24964-64-5) → (3R,4R)-3-[(3-acetoxy-4-acetoxymethylpyrrolidin-1-yl)methyl]benzamide (705060-10-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 91 percent / H₂SO₄ / 2 h / 100 °C

2: 77 percent / NaBH(OAc)3 / 1,2-dichloro-ethane / 20 °C

With sulfuric acid; sodium tris(acetoxy)borohydride; In 1,2-dichloro-ethane;

DOI:10.1021/ja038159+

Reference yield:

tert-butyl (3R,4R)-3-hydroxy-4-(hydroxymethyl)pyrrolidine-1-carboxylate (635319-09-4) → (3R,4R)-3-[(3-acetoxy-4-acetoxymethylpyrrolidin-1-yl)methyl]benzamide (705060-10-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 90 percent / pyridine / 1 h / 0 °C

2: 98 percent / HCl / dioxane; CH₂Cl₂ / 2 h / 20 °C

3: 77 percent / NaBH(OAc)3 / 1,2-dichloro-ethane / 20 °C

With pyridine; hydrogenchloride; sodium tris(acetoxy)borohydride; In 1,4-dioxane; dichloromethane; 1,2-dichloro-ethane;

DOI:10.1021/ja038159+

upstream raw materials:

3-carboxamidobenzaldehyde

3-Cyanobenzaldehyde

tert-butyl (3R,4R)-3-hydroxy-4-(hydroxymethyl)pyrrolidine-1-carboxylate

N-tert-butoxycarbonyl-(3R,4R)-3-acetoxy-4-acetoxymethylpyrrolidine

Downstream raw materials:

(3R,4R)-3-[(3-hydroxy-4-methanesulfonylmethylpyrrolidin-1-yl)methyl]benzamide

(3R,4R)-3-[(3-hydroxy-4-hydroxymethylpyrrolidin-1-yl)methyl]benzamide