1,4-bis(p-toluenesulfonyl)-1,4-diazepan-6-ol

Base Information

• Chemical Name: 1,4-bis(p-toluenesulfonyl)-1,4-diazepan-6-ol
• CAS No.: 1403590-46-4
• Molecular Formula: C₃₂H₄₆N₂O₅
• Molecular Weight: 538.728

Synonyms:1,4-bis(p-toluenesulfonyl)-1,4-diazepan-6-ol

Chemical Property of 1,4-bis(p-toluenesulfonyl)-1,4-diazepan-6-ol

Chemical Property:

Purity/Quality:

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Technology Process of 1,4-bis(p-toluenesulfonyl)-1,4-diazepan-6-ol

There total 4 articles about 1,4-bis(p-toluenesulfonyl)-1,4-diazepan-6-ol 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%

1,4-bis{[(1S,2R)-7,7-dimethyl-2-hydroxynorborn-1-yl]carbonyl}-1,4-diazepan-6-ol (1403590-45-3) + benzyl bromide (100-39-0) → 1,4-bis(p-toluenesulfonyl)-1,4-diazepan-6-ol (1403590-46-4)

Guidance literature:

1,4-bis{[(1S,2R)-7,7-dimethyl-2-hydroxynorborn-1-yl]carbonyl}-1,4-diazepan-6-ol; With 18-crown-6 ether; tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; mineral oil; for 0.25h; Inert atmosphere;

benzyl bromide; In tetrahydrofuran; mineral oil; at 20 ℃; for 18h; Inert atmosphere;

DOI:10.1002/chir.22061

Reference yield:

(1S)-(+)-ketopinic acid (464-78-8,6994-94-1,64234-14-6,40724-67-2) → 1,4-bis(p-toluenesulfonyl)-1,4-diazepan-6-ol (1403590-46-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 72 h / 20 °C

2.1: sodium tetrahydroborate / methanol / 24 h / Reflux; Inert atmosphere

3.1: 18-crown-6 ether; tetra-(n-butyl)ammonium iodide; sodium hydride / tetrahydrofuran; mineral oil / 0.25 h / Inert atmosphere

3.2: 18 h / 20 °C / Inert atmosphere

With dmap; sodium tetrahydroborate; 18-crown-6 ether; tetra-(n-butyl)ammonium iodide; sodium hydride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; methanol; dichloromethane; mineral oil;

DOI:10.1002/chir.22061

Reference yield:

6-hydroxy-1,4-diazepane-1,4-diium dibromide → 1,4-bis(p-toluenesulfonyl)-1,4-diazepan-6-ol (1403590-46-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 72 h / 20 °C

2.1: sodium tetrahydroborate / methanol / 24 h / Reflux; Inert atmosphere

3.1: 18-crown-6 ether; tetra-(n-butyl)ammonium iodide; sodium hydride / tetrahydrofuran; mineral oil / 0.25 h / Inert atmosphere

3.2: 18 h / 20 °C / Inert atmosphere

With dmap; sodium tetrahydroborate; 18-crown-6 ether; tetra-(n-butyl)ammonium iodide; sodium hydride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; methanol; dichloromethane; mineral oil;

DOI:10.1002/chir.22061

upstream raw materials:

1,4-bis{[(1S,2R)-7,7-dimethyl-2-hydroxynorborn-1-yl]carbonyl}-1,4-diazepan-6-ol

benzyl bromide

(1S)-(+)-ketopinic acid

1,4-bis{[(1S)-7,7-dimethyl-2-oxonorborn-1-yl]carbonyl}-1,4-diazepan-6-ol

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