(1S,7aS)-phenyl 3-hydroxy-1,7a-dimethyl-2-oxo-2,4,5,6,7,7a-hexahydro-1H-indene-1-carboxylate

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Chemical Name:(1S,7aS)-phenyl 3-hydroxy-1,7a-dimethyl-2-oxo-2,4,5,6,7,7a-hexahydro-1H-indene-1-carboxylate
CAS No.:1643935-83-4
Molecular Formula:C₁₈H₂₀O₄
Molecular Weight:300.354
Hs Code.:

Synonyms:(1S,7aS)-phenyl 3-hydroxy-1,7a-dimethyl-2-oxo-2,4,5,6,7,7a-hexahydro-1H-indene-1-carboxylate

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Chemical Property of (1S,7aS)-phenyl 3-hydroxy-1,7a-dimethyl-2-oxo-2,4,5,6,7,7a-hexahydro-1H-indene-1-carboxylate

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Technology Process of (1S,7aS)-phenyl 3-hydroxy-1,7a-dimethyl-2-oxo-2,4,5,6,7,7a-hexahydro-1H-indene-1-carboxylate

There total 4 articles about (1S,7aS)-phenyl 3-hydroxy-1,7a-dimethyl-2-oxo-2,4,5,6,7,7a-hexahydro-1H-indene-1-carboxylate 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: 71.0%

: 1643935-68-5
(E)-phenyl 3-(benzhydryloxy)-2-methyl-4-(2-methylcyclohex-1-en-1-yl)-4-oxobut-2-enoate

: 1643935-83-4
(1S,7aS)-phenyl 3-hydroxy-1,7a-dimethyl-2-oxo-2,4,5,6,7,7a-hexahydro-1H-indene-1-carboxylate

Guidance literature:: With 2-tert-Butylphenol; N-{(4S,11bR)-2,6-bis[4-(tert-butyl)phenyl]-4-oxidodinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin-4-yl}-1,1,1-trifluoromethanesulfonamide; In toluene; at 20 ℃; for 24h; enantioselective reaction;
DOI:10.1002/anie.201403587

Reference yield:

: 13148-94-2
2-methyl-1-cyclohexenecarboxylic acid

: 1643935-83-4
(1S,7aS)-phenyl 3-hydroxy-1,7a-dimethyl-2-oxo-2,4,5,6,7,7a-hexahydro-1H-indene-1-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1.1: oxalyl dichloride / N,N-dimethyl-formamide; toluene; dichloromethane / 20 °C / Inert atmosphere

2.1: 2,2,6,6-tetramethylpiperidinylmagnesium chloride lithium chloride complex / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere

2.2: 0.5 h / -30 °C / Inert atmosphere

2.3: -30 - 0 °C / Inert atmosphere

3.1: 2-tert-Butylphenol; N-{(4S,11bR)-2,6-bis[4-(tert-butyl)phenyl]-4-oxidodinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin-4-yl}-1,1,1-trifluoromethanesulfonamide / toluene / 24 h / 20 °C

With 2,2,6,6-tetramethylpiperidinylmagnesium chloride lithium chloride complex; oxalyl dichloride; 2-tert-Butylphenol; N-{(4S,11bR)-2,6-bis[4-(tert-butyl)phenyl]-4-oxidodinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin-4-yl}-1,1,1-trifluoromethanesulfonamide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene; 3.1: |Nazarov Cyclization;
DOI:10.1002/anie.201403587

Reference yield:

: 104654-69-5
Ethyl 2-methyl-1-cyclohex-1-ene carboxylate

: 1643935-83-4
(1S,7aS)-phenyl 3-hydroxy-1,7a-dimethyl-2-oxo-2,4,5,6,7,7a-hexahydro-1H-indene-1-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1.1: lithium hydroxide monohydrate; water / tetrahydrofuran; methanol / 20 - 70 °C

2.1: oxalyl dichloride / N,N-dimethyl-formamide; toluene; dichloromethane / 20 °C / Inert atmosphere

3.1: 2,2,6,6-tetramethylpiperidinylmagnesium chloride lithium chloride complex / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere

3.2: 0.5 h / -30 °C / Inert atmosphere

3.3: -30 - 0 °C / Inert atmosphere

4.1: 2-tert-Butylphenol; N-{(4S,11bR)-2,6-bis[4-(tert-butyl)phenyl]-4-oxidodinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin-4-yl}-1,1,1-trifluoromethanesulfonamide / toluene / 24 h / 20 °C

With 2,2,6,6-tetramethylpiperidinylmagnesium chloride lithium chloride complex; oxalyl dichloride; lithium hydroxide monohydrate; 2-tert-Butylphenol; N-{(4S,11bR)-2,6-bis[4-(tert-butyl)phenyl]-4-oxidodinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin-4-yl}-1,1,1-trifluoromethanesulfonamide; water; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; 4.1: |Nazarov Cyclization;
DOI:10.1002/anie.201403587