(2S,6R)-2-(6-((tert-butoxycarbonylamino)methyl)benzo[d][1,3]dioxol-5-yl)-6-(2-oxoethyl)cyclohexanone

Base Information

Chemical Name:(2S,6R)-2-(6-((tert-butoxycarbonylamino)methyl)benzo[d][1,3]dioxol-5-yl)-6-(2-oxoethyl)cyclohexanone
CAS No.:1448847-29-7
Molecular Formula:C₂₁H₂₇NO₆
Molecular Weight:389.448
Hs Code.:

Synonyms:(2S,6R)-2-(6-((tert-butoxycarbonylamino)methyl)benzo[d][1,3]dioxol-5-yl)-6-(2-oxoethyl)cyclohexanone

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Chemical Property of (2S,6R)-2-(6-((tert-butoxycarbonylamino)methyl)benzo[d][1,3]dioxol-5-yl)-6-(2-oxoethyl)cyclohexanone

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Technology Process of (2S,6R)-2-(6-((tert-butoxycarbonylamino)methyl)benzo[d][1,3]dioxol-5-yl)-6-(2-oxoethyl)cyclohexanone

There total 4 articles about (2S,6R)-2-(6-((tert-butoxycarbonylamino)methyl)benzo[d][1,3]dioxol-5-yl)-6-(2-oxoethyl)cyclohexanone 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: 93.0%

: 1448847-28-6
(1S,2S,6R)-2-(6-(tert-butoxycarbonylaminomethyl)benzo[d][1,3]dioxol-5-yl)-6-(2-hydroxyethyl)-cyclohexanol

: 1448847-29-7
(2S,6R)-2-(6-((tert-butoxycarbonylamino)methyl)benzo[d][1,3]dioxol-5-yl)-6-(2-oxoethyl)cyclohexanone

Guidance literature:: (1S,2S,6R)-2-(6-(tert-butoxycarbonylaminomethyl)benzo[d][1,3]dioxol-5-yl)-6-(2-hydroxyethyl)-cyclohexanol; With oxalyl dichloride; dimethyl sulfoxide; In dichloromethane; at -78 ℃; for 2.5h;

With triethylamine; In dichloromethane; at -78 - 20 ℃;
DOI:10.1002/anie.201207561

Reference yield:

: 930-68-7
cyclohexenone

: 1448847-29-7
(2S,6R)-2-(6-((tert-butoxycarbonylamino)methyl)benzo[d][1,3]dioxol-5-yl)-6-(2-oxoethyl)cyclohexanone

Guidance literature:: Multi-step reaction with 6 steps

1.1: lithium diisopropyl amide / tetrahydrofuran / 1 h / -78 °C

1.2: 2.5 h / -78 °C

2.1: iodine; potassium carbonate; dmap / water; tetrahydrofuran / 20 °C

3.1: palladium 10% on activated carbon; sodium carbonate / water; 1,2-dimethoxyethane / 12 h / 20 °C

4.1: palladium 10% on activated carbon; hydrogen / ethanol / 2 h / 35 °C / 760.05 Torr

5.1: C₆₃H₆₆Cl₂N₂P₂Ru; potassium tert-butylate; hydrogen / isopropyl alcohol / 50 h / 25 - 30 °C / 38002.6 Torr / Autoclave

6.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 2.5 h / -78 °C

6.2: -78 - 20 °C

With dmap; oxalyl dichloride; palladium 10% on activated carbon; C₆₃H₆₆Cl₂N₂P₂Ru; potassium tert-butylate; hydrogen; iodine; sodium carbonate; potassium carbonate; dimethyl sulfoxide; lithium diisopropyl amide; In tetrahydrofuran; 1,2-dimethoxyethane; ethanol; dichloromethane; water; isopropyl alcohol; 6.1: |Swern Oxidation / 6.2: |Swern Oxidation;
DOI:10.1002/anie.201207561

Reference yield:

: 111248-50-1
ethyl 2-(2-oxocyclohex-3-en-1-yl)acetate

: 1448847-29-7
(2S,6R)-2-(6-((tert-butoxycarbonylamino)methyl)benzo[d][1,3]dioxol-5-yl)-6-(2-oxoethyl)cyclohexanone

Guidance literature:: Multi-step reaction with 5 steps

1.1: iodine; potassium carbonate; dmap / water; tetrahydrofuran / 20 °C

2.1: palladium 10% on activated carbon; sodium carbonate / water; 1,2-dimethoxyethane / 12 h / 20 °C

3.1: palladium 10% on activated carbon; hydrogen / ethanol / 2 h / 35 °C / 760.05 Torr

4.1: C₆₃H₆₆Cl₂N₂P₂Ru; potassium tert-butylate; hydrogen / isopropyl alcohol / 50 h / 25 - 30 °C / 38002.6 Torr / Autoclave

5.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 2.5 h / -78 °C

5.2: -78 - 20 °C

With dmap; oxalyl dichloride; palladium 10% on activated carbon; C₆₃H₆₆Cl₂N₂P₂Ru; potassium tert-butylate; hydrogen; iodine; sodium carbonate; potassium carbonate; dimethyl sulfoxide; In tetrahydrofuran; 1,2-dimethoxyethane; ethanol; dichloromethane; water; isopropyl alcohol; 5.1: |Swern Oxidation / 5.2: |Swern Oxidation;
DOI:10.1002/anie.201207561