(4aR,7aS,9R,10aS)-2-Benzyl-9-formyl-8-hex-5-enoyl-1-oxo-1,2,3,4,4a,7,7a,8,9,10-decahydro-pyrrolo[2,3-i]isoquinoline-5-carboxylic acid methyl ester

Base Information

Chemical Name:(4aR,7aS,9R,10aS)-2-Benzyl-9-formyl-8-hex-5-enoyl-1-oxo-1,2,3,4,4a,7,7a,8,9,10-decahydro-pyrrolo[2,3-i]isoquinoline-5-carboxylic acid methyl ester
CAS No.:155530-62-4
Molecular Formula:C₂₇H₃₂N₂O₅
Molecular Weight:464.561
Hs Code.:

Synonyms:(4aR,7aS,9R,10aS)-2-Benzyl-9-formyl-8-hex-5-enoyl-1-oxo-1,2,3,4,4a,7,7a,8,9,10-decahydro-pyrrolo[2,3-i]isoquinoline-5-carboxylic acid methyl ester

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Chemical Property of (4aR,7aS,9R,10aS)-2-Benzyl-9-formyl-8-hex-5-enoyl-1-oxo-1,2,3,4,4a,7,7a,8,9,10-decahydro-pyrrolo[2,3-i]isoquinoline-5-carboxylic acid methyl ester

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Technology Process of (4aR,7aS,9R,10aS)-2-Benzyl-9-formyl-8-hex-5-enoyl-1-oxo-1,2,3,4,4a,7,7a,8,9,10-decahydro-pyrrolo[2,3-i]isoquinoline-5-carboxylic acid methyl ester

There total 21 articles about (4aR,7aS,9R,10aS)-2-Benzyl-9-formyl-8-hex-5-enoyl-1-oxo-1,2,3,4,4a,7,7a,8,9,10-decahydro-pyrrolo[2,3-i]isoquinoline-5-carboxylic acid 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: 80.0%

: 155530-61-3
methyl (2R,3aS,7aR,10aS)-5-benzyl-2-hydroxymethyl-1-(hex-5-enoyl)-4-oxo1,2,3,4,5,6,7,7a,10,10a-decahydropyrrolo[2.3-i]isoquinoline-8-carboxylate

: 155530-62-4
(4aR,7aS,9R,10aS)-2-Benzyl-9-formyl-8-hex-5-enoyl-1-oxo-1,2,3,4,4a,7,7a,8,9,10-decahydro-pyrrolo[2,3-i]isoquinoline-5-carboxylic acid methyl ester

Guidance literature:: With oxalyl dichloride; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; for 12h;
DOI:10.1016/S0040-4039(00)75792-3

Reference yield:

: 66673-40-3
(R)-5-hydroxymethylpyrrolidin-2-one

: 155530-62-4
(4aR,7aS,9R,10aS)-2-Benzyl-9-formyl-8-hex-5-enoyl-1-oxo-1,2,3,4,4a,7,7a,8,9,10-decahydro-pyrrolo[2,3-i]isoquinoline-5-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 12 steps

1.1: 95 percent / imidazole / dimethylformamide / 5 h / 20 °C

2.1: 93 percent / DMAP; triethylamine / CH₂Cl₂ / 0 - 20 °C

3.1: HMDS; n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

3.2: 99 percent / tetrahydrofuran; hexane / 0.75 h / -78 - 20 °C

4.1: 90 percent / H₂ / Pd/C / ethyl acetate / 22 h

5.1: 84 percent / NaBH₄ / HCl / ethanol / 1.47 h / -10 °C

6.1: oxalyl chloride / CH₂Cl₂ / 20 °C

7.1: 81 percent / Et₃N / benzene / 20 °C

8.1: 74 percent / toluene / 48 h / 150 °C

9.1: 76 percent / TMS-I / CH₂Cl₂ / 2.5 h / 0 - 20 °C

10.1: 81 percent / Et₃N; DMAP / benzene / 12 h / 20 °C

11.1: 93 percent / HF / pyridine; CH₂Cl₂ / 0.17 h / 0 °C

12.1: oxalyl chloride; DMSO / CH₂Cl₂ / 3 h / -63 °C

With 1H-imidazole; dmap; sodium tetrahydroborate; n-butyllithium; oxalyl dichloride; trimethylsilyl iodide; hydrogen fluoride; hydrogen; dimethyl sulfoxide; triethylamine; 1,1,1,3,3,3-hexamethyl-disilazane; hydrogenchloride; palladium on activated charcoal; In tetrahydrofuran; pyridine; ethanol; hexane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene; benzene; 8.1: intramolecular Diels-Alder reaction / 12.1: Swern oxidation;
DOI:10.1021/ja0202964

Reference yield:

: 138629-44-4
(R)-5-(tert-butyl-diphenyl-silanyloxymethyl)-pyrrolidin-2-one

: 155530-62-4
(4aR,7aS,9R,10aS)-2-Benzyl-9-formyl-8-hex-5-enoyl-1-oxo-1,2,3,4,4a,7,7a,8,9,10-decahydro-pyrrolo[2,3-i]isoquinoline-5-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 11 steps

1.1: 93 percent / DMAP; triethylamine / CH₂Cl₂ / 0 - 20 °C

2.1: HMDS; n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

2.2: 99 percent / tetrahydrofuran; hexane / 0.75 h / -78 - 20 °C

3.1: 90 percent / H₂ / Pd/C / ethyl acetate / 22 h

4.1: 84 percent / NaBH₄ / HCl / ethanol / 1.47 h / -10 °C

5.1: oxalyl chloride / CH₂Cl₂ / 20 °C

6.1: 81 percent / Et₃N / benzene / 20 °C

7.1: 74 percent / toluene / 48 h / 150 °C

8.1: 76 percent / TMS-I / CH₂Cl₂ / 2.5 h / 0 - 20 °C

9.1: 81 percent / Et₃N; DMAP / benzene / 12 h / 20 °C

10.1: 93 percent / HF / pyridine; CH₂Cl₂ / 0.17 h / 0 °C

11.1: oxalyl chloride; DMSO / CH₂Cl₂ / 3 h / -63 °C

With dmap; sodium tetrahydroborate; n-butyllithium; oxalyl dichloride; trimethylsilyl iodide; hydrogen fluoride; hydrogen; dimethyl sulfoxide; triethylamine; 1,1,1,3,3,3-hexamethyl-disilazane; hydrogenchloride; palladium on activated charcoal; In tetrahydrofuran; pyridine; ethanol; hexane; dichloromethane; ethyl acetate; toluene; benzene; 7.1: intramolecular Diels-Alder reaction / 11.1: Swern oxidation;
DOI:10.1021/ja0202964