(3R,4R)-4-benzyloxy-3-fluoro-2,3,4,7-tetrahydroazepine-1-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: (3R,4R)-4-benzyloxy-3-fluoro-2,3,4,7-tetrahydroazepine-1-carboxylic acid tert-butyl ester
• CAS No.: 1417557-65-3
• Molecular Formula: C₁₈H₂₄FNO₃
• Molecular Weight: 321.392
• Mol file: 1417557-65-3.mol

Synonyms:(3R,4R)-4-benzyloxy-3-fluoro-2,3,4,7-tetrahydroazepine-1-carboxylic acid tert-butyl ester

Chemical Property of (3R,4R)-4-benzyloxy-3-fluoro-2,3,4,7-tetrahydroazepine-1-carboxylic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4R)-4-benzyloxy-3-fluoro-2,3,4,7-tetrahydroazepine-1-carboxylic acid tert-butyl ester

There total 4 articles about (3R,4R)-4-benzyloxy-3-fluoro-2,3,4,7-tetrahydroazepine-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: 95.0%

(3S,4R)-4-benzyloxy-3-hydroxy-2,3,4,7-tetrahydroazepine-1-carboxylic acid tert-butyl ester (263889-21-0) → (3R,4R)-4-benzyloxy-3-fluoro-2,3,4,7-tetrahydroazepine-1-carboxylic acid tert-butyl ester (1417557-65-3)

Guidance literature:

With (bis-(2-methoxyethyl)amino)sulfur trufluoride; In dichloromethane; at 25 ℃; for 4h; Inert atmosphere;

DOI:10.1016/j.tet.2012.10.078

Reference yield:

(S)-2-((R)-1-benzyloxy-allyl)-oxirane (110009-21-7,115586-66-8,110044-33-2) → (3R,4R)-4-benzyloxy-3-fluoro-2,3,4,7-tetrahydroazepine-1-carboxylic acid tert-butyl ester (1417557-65-3)

Guidance literature:

Multi-step reaction with 4 steps

1: neat (no solvent) / 40 h / 70 °C

2: triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere

3: Grubbs catalyst first generation / dichloromethane / 42 h / Inert atmosphere; Reflux

4: (bis-(2-methoxyethyl)amino)sulfur trufluoride / dichloromethane / 4 h / 25 °C / Inert atmosphere

With Grubbs catalyst first generation; triethylamine; (bis-(2-methoxyethyl)amino)sulfur trufluoride; In dichloromethane;

DOI:10.1016/j.tet.2012.10.078

Reference yield:

(2S,3R)-allyl-(3-benzyloxy-2-hydroxy-pent-4-enyl)-carbamic acid tert-butyl ester (263889-20-9) → (3R,4R)-4-benzyloxy-3-fluoro-2,3,4,7-tetrahydroazepine-1-carboxylic acid tert-butyl ester (1417557-65-3)

Guidance literature:

Multi-step reaction with 2 steps

1: Grubbs catalyst first generation / dichloromethane / 42 h / Inert atmosphere; Reflux

2: (bis-(2-methoxyethyl)amino)sulfur trufluoride / dichloromethane / 4 h / 25 °C / Inert atmosphere

With Grubbs catalyst first generation; (bis-(2-methoxyethyl)amino)sulfur trufluoride; In dichloromethane;

DOI:10.1016/j.tet.2012.10.078

upstream raw materials:

(S)-2-((R)-1-benzyloxy-allyl)-oxirane

(2S,3R)-1-allylamino-3-benzyloxy-pent-4-en-2-ol

(2S,3R)-allyl-(3-benzyloxy-2-hydroxy-pent-4-enyl)-carbamic acid tert-butyl ester

(3S,4R)-4-benzyloxy-3-hydroxy-2,3,4,7-tetrahydroazepine-1-carboxylic acid tert-butyl ester