(S)-(+)-6,7-bis(benzoyloxy)-1-cyano-1-methyl-1,2,3,4-tetrahydroisoquinoline-2-carboxylic acid ethyl ester

Base Information

Chemical Name:(S)-(+)-6,7-bis(benzoyloxy)-1-cyano-1-methyl-1,2,3,4-tetrahydroisoquinoline-2-carboxylic acid ethyl ester
CAS No.:1026822-75-2
Molecular Formula:C₂₈H₂₄N₂O₆
Molecular Weight:484.508
Hs Code.:

Synonyms:(S)-(+)-6,7-bis(benzoyloxy)-1-cyano-1-methyl-1,2,3,4-tetrahydroisoquinoline-2-carboxylic acid ethyl ester

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Chemical Property of (S)-(+)-6,7-bis(benzoyloxy)-1-cyano-1-methyl-1,2,3,4-tetrahydroisoquinoline-2-carboxylic acid ethyl ester

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Technology Process of (S)-(+)-6,7-bis(benzoyloxy)-1-cyano-1-methyl-1,2,3,4-tetrahydroisoquinoline-2-carboxylic acid ethyl ester

There total 5 articles about (S)-(+)-6,7-bis(benzoyloxy)-1-cyano-1-methyl-1,2,3,4-tetrahydroisoquinoline-2-carboxylic acid ethyl 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: 38.0%

: 380427-49-6
(+)-(S)-6,7-bis(benzoyloxy)-1-cyano-1-methyl-1,2-dihydroisoquinoline-2-carboxylic acid vinyl ester

: 1026822-75-2
(S)-(+)-6,7-bis(benzoyloxy)-1-cyano-1-methyl-1,2,3,4-tetrahydroisoquinoline-2-carboxylic acid ethyl ester

Guidance literature:: With Wilkinson's catalyst; hydrogen; In ethanol; benzene; for 48h; under 68404.6 Torr;
DOI:10.1021/ja016935c

Reference yield:

: 4721-98-6
6,7-dimethoxy-1-methyl-3,4-dihydroisoquinoline

: 1026822-75-2
(S)-(+)-6,7-bis(benzoyloxy)-1-cyano-1-methyl-1,2,3,4-tetrahydroisoquinoline-2-carboxylic acid ethyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: Pd/C / various solvent(s) / 30 h / 176 °C

2: aq. HBr / 27 h / 100 °C

3: pyridine / CH₂Cl₂ / 20 °C

4: (6,6'-dibromo BINOL)AlCl / CH₂Cl₂ / 48 h / -60 °C

5: 38 percent / hydrogen; chlorotris(triphenylphosphosphine)rhodium / ethanol; benzene / 48 h / 68404.6 Torr

With pyridine; Wilkinson's catalyst; (6,6'-dibromo BINOL)AlCl; hydrogen bromide; hydrogen; palladium on activated charcoal; In ethanol; dichloromethane; benzene; 4: Reissert-type reaction;
DOI:10.1021/ja016935c

Reference yield:

: 4594-02-9
nigellimine

: 1026822-75-2
(S)-(+)-6,7-bis(benzoyloxy)-1-cyano-1-methyl-1,2,3,4-tetrahydroisoquinoline-2-carboxylic acid ethyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: aq. HBr / 27 h / 100 °C

2: pyridine / CH₂Cl₂ / 20 °C

3: (6,6'-dibromo BINOL)AlCl / CH₂Cl₂ / 48 h / -60 °C

4: 38 percent / hydrogen; chlorotris(triphenylphosphosphine)rhodium / ethanol; benzene / 48 h / 68404.6 Torr

With pyridine; Wilkinson's catalyst; (6,6'-dibromo BINOL)AlCl; hydrogen bromide; hydrogen; In ethanol; dichloromethane; benzene; 3: Reissert-type reaction;
DOI:10.1021/ja016935c