(4aR,5S,10aR)-2-Benzyl-1-oxo-2,3,4,4a,5,6,9,10-octahydro-1H-pyrrolo[2,3-i]isoquinoline-5,8-dicarboxylic acid 8-ethyl ester 5-methyl ester

Base Information

Chemical Name:(4aR,5S,10aR)-2-Benzyl-1-oxo-2,3,4,4a,5,6,9,10-octahydro-1H-pyrrolo[2,3-i]isoquinoline-5,8-dicarboxylic acid 8-ethyl ester 5-methyl ester
CAS No.:123613-50-3
Molecular Formula:C₂₃H₂₈N₂O₅
Molecular Weight:412.486
Hs Code.:

(4aR,5S,10aR)-2-Benzyl-1-oxo-2,3,4,4a,5,6,9,10-octahydro-1H-pyrrolo[2,3-i]isoquinoline-5,8-dicarboxylic acid 8-ethyl ester 5-methyl ester

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Chemical Property of (4aR,5S,10aR)-2-Benzyl-1-oxo-2,3,4,4a,5,6,9,10-octahydro-1H-pyrrolo[2,3-i]isoquinoline-5,8-dicarboxylic acid 8-ethyl ester 5-methyl ester

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Technology Process of (4aR,5S,10aR)-2-Benzyl-1-oxo-2,3,4,4a,5,6,9,10-octahydro-1H-pyrrolo[2,3-i]isoquinoline-5,8-dicarboxylic acid 8-ethyl ester 5-methyl ester

There total 10 articles about (4aR,5S,10aR)-2-Benzyl-1-oxo-2,3,4,4a,5,6,9,10-octahydro-1H-pyrrolo[2,3-i]isoquinoline-5,8-dicarboxylic acid 8-ethyl ester 5-methyl 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:

: 63656-16-6
(2-iodo-ethyl)-carbamic acid ethyl ester

: 123613-50-3
(4aR,5S,10aR)-2-Benzyl-1-oxo-2,3,4,4a,5,6,9,10-octahydro-1H-pyrrolo[2,3-i]isoquinoline-5,8-dicarboxylic acid 8-ethyl ester 5-methyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 1) NaH; 2) TsOH, quinoline / 1) DME, R_.T_., 4 days; 2) heating, 30 min

2: 49 percent / LDA / tetrahydrofuran

3: acetonitrile / 16 h / Ambient temperature

4: DBU / CH₂Cl₂ / 1 h / Ambient temperature

5: 77 percent / silver triflate, diisopropylethylamine / 16 h / Ambient temperature

6: 96 percent / toluene / 6 h / Heating

With quinoline; silver trifluoromethanesulfonate; sodium hydride; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; toluene; acetonitrile;
DOI:10.1016/S0040-4039(00)99482-6

Reference yield:

: 39896-97-4
benzyl-carbamic acid benzyl ester

: 123613-50-3
(4aR,5S,10aR)-2-Benzyl-1-oxo-2,3,4,4a,5,6,9,10-octahydro-1H-pyrrolo[2,3-i]isoquinoline-5,8-dicarboxylic acid 8-ethyl ester 5-methyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 76 percent / 16 h / Ambient temperature

2: BF₃*OEt₂ / CH₂Cl₂ / 2 h / Ambient temperature

3: 81 percent / TMSCl, NaI / acetonitrile / 5 h / Heating

4: 77 percent / silver triflate, diisopropylethylamine / 16 h / Ambient temperature

5: 96 percent / toluene / 6 h / Heating

With chloro-trimethyl-silane; boron trifluoride diethyl etherate; silver trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine; sodium iodide; In dichloromethane; toluene; acetonitrile;
DOI:10.1016/S0040-4039(00)99482-6

Reference yield:

: 119582-47-7
tert-butyl((1-methoxybuta-1,3-dien-1-yl)oxy)dimethylsilane

: 123613-50-3
(4aR,5S,10aR)-2-Benzyl-1-oxo-2,3,4,4a,5,6,9,10-octahydro-1H-pyrrolo[2,3-i]isoquinoline-5,8-dicarboxylic acid 8-ethyl ester 5-methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: BF₃*OEt₂ / CH₂Cl₂ / 2 h / Ambient temperature

2: 81 percent / TMSCl, NaI / acetonitrile / 5 h / Heating

3: 77 percent / silver triflate, diisopropylethylamine / 16 h / Ambient temperature

4: 96 percent / toluene / 6 h / Heating

With chloro-trimethyl-silane; boron trifluoride diethyl etherate; silver trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine; sodium iodide; In dichloromethane; toluene; acetonitrile;
DOI:10.1016/S0040-4039(00)99482-6