(6S,8aS)-4-Oxo-hexahydro-pyrrolo[1,2-a]pyrazine-2,6-dicarboxylic acid 2-benzyl ester 6-ethyl ester

Base Information

Chemical Name:(6S,8aS)-4-Oxo-hexahydro-pyrrolo[1,2-a]pyrazine-2,6-dicarboxylic acid 2-benzyl ester 6-ethyl ester
CAS No.:220724-83-4
Molecular Formula:C₁₈H₂₂N₂O₅
Molecular Weight:346.383
Hs Code.:

Synonyms:(6S,8aS)-4-Oxo-hexahydro-pyrrolo[1,2-a]pyrazine-2,6-dicarboxylic acid 2-benzyl ester 6-ethyl ester

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Chemical Property of (6S,8aS)-4-Oxo-hexahydro-pyrrolo[1,2-a]pyrazine-2,6-dicarboxylic acid 2-benzyl ester 6-ethyl ester

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Technology Process of (6S,8aS)-4-Oxo-hexahydro-pyrrolo[1,2-a]pyrazine-2,6-dicarboxylic acid 2-benzyl ester 6-ethyl ester

There total 9 articles about (6S,8aS)-4-Oxo-hexahydro-pyrrolo[1,2-a]pyrazine-2,6-dicarboxylic acid 2-benzyl ester 6-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: 95.0%

: (2S,5S)-5-[(Benzyloxycarbonyl-carboxymethyl-amino)-methyl]-pyrrolidine-2-carboxylic acid ethyl ester

: 220724-83-4
(6S,8aS)-4-Oxo-hexahydro-pyrrolo[1,2-a]pyrazine-2,6-dicarboxylic acid 2-benzyl ester 6-ethyl ester

Guidance literature:: With 4-methyl-morpholine; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; In N,N-dimethyl-formamide;
DOI:10.1016/S0960-894X(98)00550-2

Reference yield:

: 501-53-1,94274-21-2
benzyl chloroformate

: 220724-83-4
(6S,8aS)-4-Oxo-hexahydro-pyrrolo[1,2-a]pyrazine-2,6-dicarboxylic acid 2-benzyl ester 6-ethyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 90 percent / NMM / tetrahydrofuran / -78 - 20 °C

2: 100 percent / 4 N HCl / dioxane

3: 95 percent / BOP, NMM / dimethylformamide

With 4-methyl-morpholine; hydrogenchloride; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; In tetrahydrofuran; 1,4-dioxane; N,N-dimethyl-formamide;
DOI:10.1016/S0960-894X(98)00550-2

Reference yield:

: 144978-35-8,144978-12-1,251924-83-1
(S)-ethyl N-tert-butoxycarbonylpyroglutamate

: 220724-83-4
(6S,8aS)-4-Oxo-hexahydro-pyrrolo[1,2-a]pyrazine-2,6-dicarboxylic acid 2-benzyl ester 6-ethyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: p-TsOH

2: BF₃*OEt₂, CuBr*SMe₂ / diethyl ether; tetrahydrofuran / -78 °C

3: 1.) O₃, 2.) Me₂S / 1.) CH₂Cl₂, -78 deg C, 2.) CH₂Cl₂

4: 90 percent / NaBH₃CN / methanol / 0 - 20 °C

5: 90 percent / NMM / tetrahydrofuran / -78 - 20 °C

6: 100 percent / 4 N HCl / dioxane

7: 95 percent / BOP, NMM / dimethylformamide

With 4-methyl-morpholine; hydrogenchloride; copper(I) bromide dimethylsulfide complex; dimethylsulfide; boron trifluoride diethyl etherate; sodium cyanoborohydride; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; toluene-4-sulfonic acid; ozone; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; N,N-dimethyl-formamide;
DOI:10.1016/S0960-894X(98)00550-2