(3R)-3-[2-(4-chlorophenyl)-2-oxoethyl]-2-[(1S,5R)-5,8,8-trimethyl-2-oxo-3-oxabicyclo[3.2.1]octane-1-carbonyl]-2,3-dihydroisoindol-1-one

Base Information

Chemical Name:(3R)-3-[2-(4-chlorophenyl)-2-oxoethyl]-2-[(1S,5R)-5,8,8-trimethyl-2-oxo-3-oxabicyclo[3.2.1]octane-1-carbonyl]-2,3-dihydroisoindol-1-one
CAS No.:944052-55-5
Molecular Formula:C₂₇H₂₆ClNO₅
Molecular Weight:479.96
Hs Code.:

Synonyms:(3R)-3-[2-(4-chlorophenyl)-2-oxoethyl]-2-[(1S,5R)-5,8,8-trimethyl-2-oxo-3-oxabicyclo[3.2.1]octane-1-carbonyl]-2,3-dihydroisoindol-1-one

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Chemical Property of (3R)-3-[2-(4-chlorophenyl)-2-oxoethyl]-2-[(1S,5R)-5,8,8-trimethyl-2-oxo-3-oxabicyclo[3.2.1]octane-1-carbonyl]-2,3-dihydroisoindol-1-one

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Technology Process of (3R)-3-[2-(4-chlorophenyl)-2-oxoethyl]-2-[(1S,5R)-5,8,8-trimethyl-2-oxo-3-oxabicyclo[3.2.1]octane-1-carbonyl]-2,3-dihydroisoindol-1-one

There total 1 articles about (3R)-3-[2-(4-chlorophenyl)-2-oxoethyl]-2-[(1S,5R)-5,8,8-trimethyl-2-oxo-3-oxabicyclo[3.2.1]octane-1-carbonyl]-2,3-dihydroisoindol-1-one 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: 46.0%

: 944052-49-7
3-bromo-2-[(1S,5R)-5,8,8-trimethyl-2-oxo-3-oxabicyclo[3.2.1]octane-1-carbonyl]-2,3-dihydroisoindol-1-one

: 58518-76-6
((1-(4-chlorophenyl)vinyl)oxy)trimethylsilane

: 944052-55-5
(3R)-3-[2-(4-chlorophenyl)-2-oxoethyl]-2-[(1S,5R)-5,8,8-trimethyl-2-oxo-3-oxabicyclo[3.2.1]octane-1-carbonyl]-2,3-dihydroisoindol-1-one

: 944052-52-2
(3S)-3-[2-(4-chlorophenyl)-2-oxoethyl]-2-[(1S,5R)-5,8,8-trimethyl-2-oxo-3-oxabicyclo[3.2.1]octane-1-carbonyl]-2,3-dihydroisoindol-1-one

Guidance literature:: With mercury(II) iodide; In dichloromethane; at 20 ℃; for 5h;
DOI:10.1002/jhet.5570440312

Reference yield: 84.0%

: 944052-55-5
(3R)-3-[2-(4-chlorophenyl)-2-oxoethyl]-2-[(1S,5R)-5,8,8-trimethyl-2-oxo-3-oxabicyclo[3.2.1]octane-1-carbonyl]-2,3-dihydroisoindol-1-one

: 1338225-76-5
(3R)-3-[(2S)-2-hydroxy-2-(4-chlorophenyl)ethyl]-2-[(1S,5R)-5,8,8-trimethyl-2-oxo-3-oxabicyclo[3.2.1]octane-1-carbonyl]-2,3-dihydroisoindol-1-one

: 1338225-94-7
(3R)-3-[(2R)-2-hydroxy-2-(4-chlorophenyl)ethyl]-2-[(1S,5R)-5,8,8-trimethyl-2-oxo-3-oxabicyclo[3.2.1]octane-1-carbonyl]-2,3-dihydroisoindol-1-one

Guidance literature:: With Li[Al(tBuO)3H]; In tetrahydrofuran; at 0 ℃; for 16h; optical yield given as %de; Inert atmosphere;
DOI:10.1016/j.bmcl.2011.07.119

Reference yield:

: 944052-55-5
(3R)-3-[2-(4-chlorophenyl)-2-oxoethyl]-2-[(1S,5R)-5,8,8-trimethyl-2-oxo-3-oxabicyclo[3.2.1]octane-1-carbonyl]-2,3-dihydroisoindol-1-one

: 1338225-83-4
{(1R)-2-[(1R)-3-oxo-2,3-dihydro-1H-isoindol-1-yl]-1-(4-chlorphenyl)ethyl} benzoate

Guidance literature:: Multi-step reaction with 3 steps

1.1: Li[Al(tBuO)3H] / tetrahydrofuran / 16 h / 0 °C / Inert atmosphere

2.1: lithium borohydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

3.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

3.2: 0 °C / Inert atmosphere

With lithium borohydride; di-isopropyl azodicarboxylate; Li[Al(tBuO)3H]; triphenylphosphine; In tetrahydrofuran; 3.1: Mitsunobu reaction / 3.2: Mitsunobu reaction;
DOI:10.1016/j.bmcl.2011.07.119