(4aR,6S,8aS)-6-(2-Bromo-ethyl)-2,2-dimethyl-5-(toluene-4-sulfonyl)-hexahydro-[1,3]dioxino[5,4-b]pyridine

Base Information

• Chemical Name: (4aR,6S,8aS)-6-(2-Bromo-ethyl)-2,2-dimethyl-5-(toluene-4-sulfonyl)-hexahydro-[1,3]dioxino[5,4-b]pyridine
• CAS No.: 112547-25-8
• Molecular Formula: C₁₈H₂₆BrNO₄S
• Molecular Weight: 432.379

Synonyms:(4aR,6S,8aS)-6-(2-Bromo-ethyl)-2,2-dimethyl-5-(toluene-4-sulfonyl)-hexahydro-[1,3]dioxino[5,4-b]pyridine

Chemical Property of (4aR,6S,8aS)-6-(2-Bromo-ethyl)-2,2-dimethyl-5-(toluene-4-sulfonyl)-hexahydro-[1,3]dioxino[5,4-b]pyridine

Chemical Property:

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Technology Process of (4aR,6S,8aS)-6-(2-Bromo-ethyl)-2,2-dimethyl-5-(toluene-4-sulfonyl)-hexahydro-[1,3]dioxino[5,4-b]pyridine

There total 3 articles about (4aR,6S,8aS)-6-(2-Bromo-ethyl)-2,2-dimethyl-5-(toluene-4-sulfonyl)-hexahydro-[1,3]dioxino[5,4-b]pyridine 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: 92.0%

2-[(4aR,6S,8aS)-2,2-Dimethyl-5-(toluene-4-sulfonyl)-hexahydro-[1,3]dioxino[5,4-b]pyridin-6-yl]-ethanol (96839-07-5) → (4aR,6S,8aS)-6-(2-Bromo-ethyl)-2,2-dimethyl-5-(toluene-4-sulfonyl)-hexahydro-[1,3]dioxino[5,4-b]pyridine (112547-25-8)

Guidance literature:

With N-Bromosuccinimide; triphenylphosphine;

DOI:10.1016/S0040-4039(01)80997-7

Reference yield:

(1S,3S,4S)-5-Oxo-2-(toluene-4-sulfonyl)-2-aza-bicyclo[2.2.2]octane-3-carboxylic acid methyl ester (96839-05-3,96894-87-0) → (4aR,6S,8aS)-6-(2-Bromo-ethyl)-2,2-dimethyl-5-(toluene-4-sulfonyl)-hexahydro-[1,3]dioxino[5,4-b]pyridine (112547-25-8)

Guidance literature:

Multi-step reaction with 2 steps

2: 92 percent / Ph₃P, NBS

With N-Bromosuccinimide; triphenylphosphine;

DOI:10.1016/S0040-4039(01)80997-7

Reference yield:

Methyl N-(p-tolylsulfonyl)iminoacetate (89366-20-1) → (4aR,6S,8aS)-6-(2-Bromo-ethyl)-2,2-dimethyl-5-(toluene-4-sulfonyl)-hexahydro-[1,3]dioxino[5,4-b]pyridine (112547-25-8)

Guidance literature:

Multi-step reaction with 3 steps

3: 92 percent / Ph₃P, NBS

With N-Bromosuccinimide; triphenylphosphine;

DOI:10.1016/S0040-4039(01)80997-7

upstream raw materials:

2-[(4aR,6S,8aS)-2,2-Dimethyl-5-(toluene-4-sulfonyl)-hexahydro-[1,3]dioxino[5,4-b]pyridin-6-yl]-ethanol

(1S,3S,4S)-5-Oxo-2-(toluene-4-sulfonyl)-2-aza-bicyclo[2.2.2]octane-3-carboxylic acid methyl ester

Methyl N-(p-tolylsulfonyl)iminoacetate

Downstream raw materials:

(4aR,6S,8aS)-6-[3-Benzenesulfonyl-7-(2-butyl-[1,3]dioxolan-2-yl)-heptyl]-2,2-dimethyl-5-(toluene-4-sulfonyl)-hexahydro-[1,3]dioxino[5,4-b]pyridine

(4aR,6S,8aS)-6-[3-Benzenesulfonyl-6-(2-pentyl-[1,3]dioxolan-2-yl)-hexyl]-2,2-dimethyl-5-(toluene-4-sulfonyl)-hexahydro-[1,3]dioxino[5,4-b]pyridine

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