(4S,7R,8aR)-4,7-Dibenzyl-6-oxo-octahydro-pyrrolo[1,2-a]pyrazine-7-carboxylic acid methyl ester

Base Information

Chemical Name:(4S,7R,8aR)-4,7-Dibenzyl-6-oxo-octahydro-pyrrolo[1,2-a]pyrazine-7-carboxylic acid methyl ester
CAS No.:184847-52-7
Molecular Formula:C₂₃H₂₆N₂O₃
Molecular Weight:378.471
Hs Code.:

Synonyms:(4S,7R,8aR)-4,7-Dibenzyl-6-oxo-octahydro-pyrrolo[1,2-a]pyrazine-7-carboxylic acid methyl ester

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Chemical Property of (4S,7R,8aR)-4,7-Dibenzyl-6-oxo-octahydro-pyrrolo[1,2-a]pyrazine-7-carboxylic acid methyl ester

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Technology Process of (4S,7R,8aR)-4,7-Dibenzyl-6-oxo-octahydro-pyrrolo[1,2-a]pyrazine-7-carboxylic acid methyl ester

There total 16 articles about (4S,7R,8aR)-4,7-Dibenzyl-6-oxo-octahydro-pyrrolo[1,2-a]pyrazine-7-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: 95.0%

: 184847-72-1
(4S,7R,8aR)-4,7-Dibenzyl-6-oxo-hexahydro-pyrrolo[1,2-a]pyrazine-2,7-dicarboxylic acid 2-tert-butyl ester 7-methyl ester

: 184847-52-7
(4S,7R,8aR)-4,7-Dibenzyl-6-oxo-octahydro-pyrrolo[1,2-a]pyrazine-7-carboxylic acid methyl ester

Guidance literature:: With trifluoroacetic acid; In dichloromethane; for 1h; Ambient temperature;
DOI:10.1016/0040-4020(96)00842-3

Reference yield:

: 59830-60-3
benzyl (1S)-(1-formyl-2-phenylethyl)carbamate

: 184847-52-7
(4S,7R,8aR)-4,7-Dibenzyl-6-oxo-octahydro-pyrrolo[1,2-a]pyrazine-7-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 13 steps

1: Et₃N / methanol / 0.25 h / Ambient temperature; 4A molecular sieves

2: NaBH₃CN, ZnCl₂ / methanol / 2.5 h / Ambient temperature

3: 74 percent / Et₃N, DMAP / CH₂Cl₂ / 24 h / Ambient temperature

4: 85 percent / aq. NaOH / methanol / 20 h / Ambient temperature

5: N-methylmorpholine / tetrahydrofuran / 0.25 h / -20 °C

6: CH₂Cl₂; diethyl ether / 0.5 h / -20 °C

7: HCl / CH₂Cl₂; methanol; diethyl ether / -20 °C

8: NaI / tetrahydrofuran / 0.17 h / Ambient temperature

9: tetrahydrofuran / 3 h / Ambient temperature

10: H₂ / Pd/C / methanol / 29 h / 1551.4 Torr / Ambient temperature

11: toluene / 72 h / Heating

12: 1.) NaOMe / 1.) THF, 5 min, 2.) THF, 1 h

13: 95 percent / TFA / CH₂Cl₂ / 1 h / Ambient temperature

With 4-methyl-morpholine; hydrogenchloride; dmap; sodium hydroxide; hydrogen; sodium methylate; sodium cyanoborohydride; triethylamine; trifluoroacetic acid; sodium iodide; zinc(II) chloride; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; toluene;
DOI:10.1016/0040-4020(96)00842-3

Reference yield:

: 128421-87-4
Z-PheΨGly-OMe

: 184847-52-7
(4S,7R,8aR)-4,7-Dibenzyl-6-oxo-octahydro-pyrrolo[1,2-a]pyrazine-7-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 11 steps

1: 74 percent / Et₃N, DMAP / CH₂Cl₂ / 24 h / Ambient temperature

2: 85 percent / aq. NaOH / methanol / 20 h / Ambient temperature

3: N-methylmorpholine / tetrahydrofuran / 0.25 h / -20 °C

4: CH₂Cl₂; diethyl ether / 0.5 h / -20 °C

5: HCl / CH₂Cl₂; methanol; diethyl ether / -20 °C

6: NaI / tetrahydrofuran / 0.17 h / Ambient temperature

7: tetrahydrofuran / 3 h / Ambient temperature

8: H₂ / Pd/C / methanol / 29 h / 1551.4 Torr / Ambient temperature

9: toluene / 72 h / Heating

10: 1.) NaOMe / 1.) THF, 5 min, 2.) THF, 1 h

11: 95 percent / TFA / CH₂Cl₂ / 1 h / Ambient temperature

With 4-methyl-morpholine; hydrogenchloride; dmap; sodium hydroxide; hydrogen; sodium methylate; triethylamine; trifluoroacetic acid; sodium iodide; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; toluene;
DOI:10.1016/0040-4020(96)00842-3