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

Base Information

Chemical Name:(1S,2S,6R)-2-(6-(tert-butoxycarbonylaminomethyl)benzo[d][1,3]dioxol-5-yl)-6-(2-hydroxyethyl)-cyclohexanol
CAS No.:1448847-28-6
Molecular Formula:C₂₁H₃₁NO₆
Molecular Weight:393.48
Hs Code.:

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

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Chemical Property of (1S,2S,6R)-2-(6-(tert-butoxycarbonylaminomethyl)benzo[d][1,3]dioxol-5-yl)-6-(2-hydroxyethyl)-cyclohexanol

Chemical Property:

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Technology Process of (1S,2S,6R)-2-(6-(tert-butoxycarbonylaminomethyl)benzo[d][1,3]dioxol-5-yl)-6-(2-hydroxyethyl)-cyclohexanol

There total 6 articles about (1S,2S,6R)-2-(6-(tert-butoxycarbonylaminomethyl)benzo[d][1,3]dioxol-5-yl)-6-(2-hydroxyethyl)-cyclohexanol 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%

: 2-(6-(tert-butoxycarbonylaminomethyl)benzo[d][1,3]dioxol-5-yl)-6-(ethoxycarbonylmethyl)cyclohexanone

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

Guidance literature:: With C₆₃H₆₆Cl₂N₂P₂Ru; potassium tert-butylate; hydrogen; In isopropyl alcohol; at 25 - 30 ℃; for 50h; under 38002.6 Torr; enantioselective reaction; Autoclave;
DOI:10.1002/anie.201207561

Reference yield:

: 930-68-7
cyclohexenone

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

Guidance literature:: Multi-step reaction with 5 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

With dmap; palladium 10% on activated carbon; C₆₃H₆₆Cl₂N₂P₂Ru; potassium tert-butylate; hydrogen; iodine; sodium carbonate; potassium carbonate; lithium diisopropyl amide; In tetrahydrofuran; 1,2-dimethoxyethane; ethanol; water; isopropyl alcohol;
DOI:10.1002/anie.201207561

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 4 steps

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

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

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

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

With dmap; palladium 10% on activated carbon; C₆₃H₆₆Cl₂N₂P₂Ru; potassium tert-butylate; hydrogen; iodine; sodium carbonate; potassium carbonate; In tetrahydrofuran; 1,2-dimethoxyethane; ethanol; water; isopropyl alcohol;
DOI:10.1002/anie.201207561