(-)-4,7a-dimethyl-6-(naphthalen-2-yloxy)-2-(toluene-4-sulfonyl)-2,3,5,7a-tetrahydro-1H-isoindole-5-carboxylic acid naphthalen-2-yl ester

Base Information

Chemical Name:(-)-4,7a-dimethyl-6-(naphthalen-2-yloxy)-2-(toluene-4-sulfonyl)-2,3,5,7a-tetrahydro-1H-isoindole-5-carboxylic acid naphthalen-2-yl ester
CAS No.:1415125-84-6
Molecular Formula:C₃₈H₃₃NO₅S
Molecular Weight:615.75
Hs Code.:

Synonyms:(-)-4,7a-dimethyl-6-(naphthalen-2-yloxy)-2-(toluene-4-sulfonyl)-2,3,5,7a-tetrahydro-1H-isoindole-5-carboxylic acid naphthalen-2-yl ester

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Chemical Property of (-)-4,7a-dimethyl-6-(naphthalen-2-yloxy)-2-(toluene-4-sulfonyl)-2,3,5,7a-tetrahydro-1H-isoindole-5-carboxylic acid naphthalen-2-yl ester

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Technology Process of (-)-4,7a-dimethyl-6-(naphthalen-2-yloxy)-2-(toluene-4-sulfonyl)-2,3,5,7a-tetrahydro-1H-isoindole-5-carboxylic acid naphthalen-2-yl ester

There total 3 articles about (-)-4,7a-dimethyl-6-(naphthalen-2-yloxy)-2-(toluene-4-sulfonyl)-2,3,5,7a-tetrahydro-1H-isoindole-5-carboxylic acid naphthalen-2-yl ester 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: 51.0%

: 1173788-47-0
N-but-2-ynyl-2-nitro-N-(2-oxoethyl)benzenesulfonamide

: 2-(ethynyloxy)-naphthalene

: 1415125-84-6
(-)-4,7a-dimethyl-6-(naphthalen-2-yloxy)-2-(toluene-4-sulfonyl)-2,3,5,7a-tetrahydro-1H-isoindole-5-carboxylic acid naphthalen-2-yl ester

: 1415125-85-7
(+)-4,7a-dimethyl-6-(naphthalen-2-yloxy)-2-(toluene-4-sulfonyl)-2,3,5,7a-tetrahydro-1H-isoindole-5-carboxylic acid naphthalen-2-yl ester

Guidance literature:: With bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; hydrogen; (R)-(+)-2,2'-bis(diphenylphosphanyl)-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl; In dichloromethane; at 80 ℃; for 72h; Inert atmosphere; Schlenk technique;
DOI:10.1021/ol3027158

Reference yield:

: 856409-63-7
N-(but-2-ynyl)-4-methyl-N-(2-oxoethyl)-benzenesulfonamide

: 1415125-84-6
(-)-4,7a-dimethyl-6-(naphthalen-2-yloxy)-2-(toluene-4-sulfonyl)-2,3,5,7a-tetrahydro-1H-isoindole-5-carboxylic acid naphthalen-2-yl ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: tetrahydrofuran; diethyl ether / 4 h / 0 - 20 °C / Inert atmosphere

2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1.5 h / -78 °C / Inert atmosphere

2.2: 3 h / -78 - 20 °C / Inert atmosphere

3.1: (R)-(+)-2,2'-bis(diphenylphosphanyl)-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl; bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; hydrogen / dichloromethane / 72 h / 80 °C / Inert atmosphere; Schlenk technique

With oxalyl dichloride; bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; hydrogen; dimethyl sulfoxide; (R)-(+)-2,2'-bis(diphenylphosphanyl)-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl; In tetrahydrofuran; diethyl ether; dichloromethane;
DOI:10.1021/ol3027158

Reference yield:

: 1173788-48-1
N-but-2-ynyl-N-(2-hydroxypropyl)-4-methylbenzenesulfon-amide

: 1415125-84-6
(-)-4,7a-dimethyl-6-(naphthalen-2-yloxy)-2-(toluene-4-sulfonyl)-2,3,5,7a-tetrahydro-1H-isoindole-5-carboxylic acid naphthalen-2-yl ester

Guidance literature:: Multi-step reaction with 2 steps

1.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1.5 h / -78 °C / Inert atmosphere

1.2: 3 h / -78 - 20 °C / Inert atmosphere

2.1: (R)-(+)-2,2'-bis(diphenylphosphanyl)-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl; bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; hydrogen / dichloromethane / 72 h / 80 °C / Inert atmosphere; Schlenk technique

With oxalyl dichloride; bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; hydrogen; dimethyl sulfoxide; (R)-(+)-2,2'-bis(diphenylphosphanyl)-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl; In dichloromethane;
DOI:10.1021/ol3027158