tert-butyl (2S)-2-{[(3aS,6S,6aR)-6-methyl-4-(4-nitrophenyl)-5-oxohexahydropyrrolo[3,2-b]pyrrol-1(2H)-yl]carbonyl}pyrrolidine-1-carboxylate

Base Information

Chemical Name:tert-butyl (2S)-2-{[(3aS,6S,6aR)-6-methyl-4-(4-nitrophenyl)-5-oxohexahydropyrrolo[3,2-b]pyrrol-1(2H)-yl]carbonyl}pyrrolidine-1-carboxylate
CAS No.:628725-82-6
Molecular Formula:C₂₃H₃₀N₄O₆
Molecular Weight:458.514
Hs Code.:

Synonyms:tert-butyl (2S)-2-{[(3aS,6S,6aR)-6-methyl-4-(4-nitrophenyl)-5-oxohexahydropyrrolo[3,2-b]pyrrol-1(2H)-yl]carbonyl}pyrrolidine-1-carboxylate

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Chemical Property of tert-butyl (2S)-2-{[(3aS,6S,6aR)-6-methyl-4-(4-nitrophenyl)-5-oxohexahydropyrrolo[3,2-b]pyrrol-1(2H)-yl]carbonyl}pyrrolidine-1-carboxylate

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Technology Process of tert-butyl (2S)-2-{[(3aS,6S,6aR)-6-methyl-4-(4-nitrophenyl)-5-oxohexahydropyrrolo[3,2-b]pyrrol-1(2H)-yl]carbonyl}pyrrolidine-1-carboxylate

There total 5 articles about tert-butyl (2S)-2-{[(3aS,6S,6aR)-6-methyl-4-(4-nitrophenyl)-5-oxohexahydropyrrolo[3,2-b]pyrrol-1(2H)-yl]carbonyl}pyrrolidine-1-carboxylate 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: 65.0%

: 586-78-7
para-nitrophenyl bromide

: 214337-23-2
tert-butyl (2S)-2-{[(3aS,6S,6aR)-6-methyl-5-oxohexahydropyrrolo[3,2-b]pyrrol-1(2H)-yl]carbonyl}pyrrolidine-1-carboxylate

: 628725-82-6
tert-butyl (2S)-2-{[(3aS,6S,6aR)-6-methyl-4-(4-nitrophenyl)-5-oxohexahydropyrrolo[3,2-b]pyrrol-1(2H)-yl]carbonyl}pyrrolidine-1-carboxylate

Guidance literature:: With potassium carbonate; copper(l) chloride; In para-xylene; Heating;
DOI:10.1021/jm030810w

Reference yield:

: 1148-11-4
N-Benzyloxycarbonyl-L-proline

: 628725-82-6
tert-butyl (2S)-2-{[(3aS,6S,6aR)-6-methyl-4-(4-nitrophenyl)-5-oxohexahydropyrrolo[3,2-b]pyrrol-1(2H)-yl]carbonyl}pyrrolidine-1-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1.1: 1-hydroxybenzotriazole hydrate; TBTU; diisopropylethylamine / acetonitrile / 0.33 h

1.2: 88.5 percent / acetonitrile; dimethylformamide / 24 h / 20 °C

2.1: 98 percent / TFA / CH₂Cl₂ / 0.75 h / 20 °C

3.1: 77 percent / H₂ / Pd/C / propan-2-ol; H₂O / 5 h / 20 °C

4.1: 65 percent / CuCl; K₂CO₃; TDA-1 / p-xylene / Heating

With hydrogen; potassium carbonate; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; 1-hydroxybenzotriazol-hydrate; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; copper(l) chloride; palladium on activated charcoal; In dichloromethane; para-xylene; water; isopropyl alcohol; acetonitrile;
DOI:10.1021/jm030810w

Reference yield:

: 214337-21-0
benzyl (2S)-2-{[(3aS,6S,6aR)-6-methyl-5-oxohexahydropyrrolo[3,2-b]pyrrol-1(2H)-yl]carbonyl}pyrrolidine-1-carboxylate

: 628725-82-6
tert-butyl (2S)-2-{[(3aS,6S,6aR)-6-methyl-4-(4-nitrophenyl)-5-oxohexahydropyrrolo[3,2-b]pyrrol-1(2H)-yl]carbonyl}pyrrolidine-1-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1: 77 percent / H₂ / Pd/C / propan-2-ol; H₂O / 5 h / 20 °C

2: 65 percent / CuCl; K₂CO₃; TDA-1 / p-xylene / Heating

With hydrogen; potassium carbonate; copper(l) chloride; palladium on activated charcoal; In para-xylene; water; isopropyl alcohol;
DOI:10.1021/jm030810w