(3aR,6aR)-(3S)-(1H-indol-3-yl)-hexahydro-pyrrolo[3,2-b]pyrrole-1,4-dicarboxylic acid 1-benzyl ester 4-tert-butyl ester

Base Information

Chemical Name:(3aR,6aR)-(3S)-(1H-indol-3-yl)-hexahydro-pyrrolo[3,2-b]pyrrole-1,4-dicarboxylic acid 1-benzyl ester 4-tert-butyl ester
CAS No.:1218929-56-6
Molecular Formula:C₂₇H₃₁N₃O₄
Molecular Weight:461.561
Hs Code.:

Synonyms:(3aR,6aR)-(3S)-(1H-indol-3-yl)-hexahydro-pyrrolo[3,2-b]pyrrole-1,4-dicarboxylic acid 1-benzyl ester 4-tert-butyl ester

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Chemical Property of (3aR,6aR)-(3S)-(1H-indol-3-yl)-hexahydro-pyrrolo[3,2-b]pyrrole-1,4-dicarboxylic acid 1-benzyl ester 4-tert-butyl ester

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Technology Process of (3aR,6aR)-(3S)-(1H-indol-3-yl)-hexahydro-pyrrolo[3,2-b]pyrrole-1,4-dicarboxylic acid 1-benzyl ester 4-tert-butyl ester

There total 11 articles about (3aR,6aR)-(3S)-(1H-indol-3-yl)-hexahydro-pyrrolo[3,2-b]pyrrole-1,4-dicarboxylic acid 1-benzyl ester 4-tert-butyl 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:

: 1218929-55-5
(3aR,6aR)-(6S)-(1H-indol-3-yl)-hexahydro-pyrrolo[3,2-b]pyrrole-1-carboxylic acid tert-butyl ester

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

: 1218929-56-6
(3aR,6aR)-(3S)-(1H-indol-3-yl)-hexahydro-pyrrolo[3,2-b]pyrrole-1,4-dicarboxylic acid 1-benzyl ester 4-tert-butyl ester

Guidance literature:: In dichloromethane; at 0 ℃; for 2h;

Reference yield:

: 850003-05-3
(2S,3S)-N-tert-butyloxycarbonyl-3-(tert-butyldimethylsilyloxy)-2-pyrrolidinecarboxylic acid methyl ester

: 1218929-56-6
(3aR,6aR)-(3S)-(1H-indol-3-yl)-hexahydro-pyrrolo[3,2-b]pyrrole-1,4-dicarboxylic acid 1-benzyl ester 4-tert-butyl ester

Guidance literature:: Multi-step reaction with 9 steps

1.1: lithium borohydride / tetrahydrofuran / 0 - 20 °C

2.1: pyridine-SO₃ complex; triethylamine / dichloromethane; dimethyl sulfoxide / 2 h / 0 - 20 °C

3.1: triethylamine / 12 h

3.2: 1 h / -78 °C

3.3: 1 h / -78 °C

4.1: silica gel; sodium iodide / cerium(III) chloride heptahydrate / acetonitrile / 0.5 h / 20 °C

5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 16 h / 0 °C

6.1: N-ethyl-N,N-diisopropylamine / dmap / dichloromethane / 1 h / 0 °C

7.1: hydrogen / palladium 10% on activated carbon / ethanol / 16 h / 2844.39 Torr

8.1: sodium acetate / ethanol / 3 h / Reflux

9.1: dichloromethane / 2 h / 0 °C

With lithium borohydride; pyridine-SO₃ complex; tetrabutyl ammonium fluoride; hydrogen; sodium acetate; silica gel; triethylamine; N-ethyl-N,N-diisopropylamine; sodium iodide; dmap; cerium(III) chloride heptahydrate; palladium 10% on activated carbon; In tetrahydrofuran; ethanol; dichloromethane; dimethyl sulfoxide; acetonitrile;

Reference yield:

: 757247-71-5
tert-butyl (2S,3S)-3-{[tert-butyl(dimethyl)silyl]oxy}-2-formylpyrrolidine-1-carboxylate

: 1218929-56-6
(3aR,6aR)-(3S)-(1H-indol-3-yl)-hexahydro-pyrrolo[3,2-b]pyrrole-1,4-dicarboxylic acid 1-benzyl ester 4-tert-butyl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: triethylamine / 12 h

1.2: 1 h / -78 °C

1.3: 1 h / -78 °C

2.1: silica gel; sodium iodide / cerium(III) chloride heptahydrate / acetonitrile / 0.5 h / 20 °C

3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 16 h / 0 °C

4.1: N-ethyl-N,N-diisopropylamine / dmap / dichloromethane / 1 h / 0 °C

5.1: hydrogen / palladium 10% on activated carbon / ethanol / 16 h / 2844.39 Torr

6.1: sodium acetate / ethanol / 3 h / Reflux

7.1: dichloromethane / 2 h / 0 °C

With tetrabutyl ammonium fluoride; hydrogen; sodium acetate; silica gel; triethylamine; N-ethyl-N,N-diisopropylamine; sodium iodide; dmap; cerium(III) chloride heptahydrate; palladium 10% on activated carbon; In tetrahydrofuran; ethanol; dichloromethane; acetonitrile;