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

Base Information

Chemical Name:(3aR,6aR)-4-(2-tert-butoxycarbonylamino-(2S)-cyclohexyl-acetyl)-(3S)-(1H-indol-3-yl)-hexahydro-pyrrolo[3,2-b]pyrrole-1-carboxylic acid benzyl ester
CAS No.:1218929-58-8
Molecular Formula:C₃₅H₄₄N₄O₅
Molecular Weight:600.758
Hs Code.:

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

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

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

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

There total 14 articles about (3aR,6aR)-4-(2-tert-butoxycarbonylamino-(2S)-cyclohexyl-acetyl)-(3S)-(1H-indol-3-yl)-hexahydro-pyrrolo[3,2-b]pyrrole-1-carboxylic acid benzyl 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:

: 1218929-57-7
(3aR,6aR)-(3S)-(1H-indol-3-yl)-hexahydro-pyrrolo[3,2-b]pyrrole-1-carboxylic acid benzyl ester

: 109183-71-3
N-(tert-butoxycarbonyl)-L-cyclohexylglycine

: 1218929-58-8
(3aR,6aR)-4-(2-tert-butoxycarbonylamino-(2S)-cyclohexyl-acetyl)-(3S)-(1H-indol-3-yl)-hexahydro-pyrrolo[3,2-b]pyrrole-1-carboxylic acid benzyl ester

Guidance literature:: With N-ethyl-N,N-diisopropylamine; HATU; In 1-methyl-pyrrolidin-2-one; at 0 - 20 ℃;

Reference yield:

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

: 1218929-58-8
(3aR,6aR)-4-(2-tert-butoxycarbonylamino-(2S)-cyclohexyl-acetyl)-(3S)-(1H-indol-3-yl)-hexahydro-pyrrolo[3,2-b]pyrrole-1-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 11 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

10.1: trifluoroacetic acid / dichloromethane / 2 h / 0 °C

11.1: N-ethyl-N,N-diisopropylamine; HATU / 1-methyl-pyrrolidin-2-one / 0 - 20 °C

With lithium borohydride; pyridine-SO₃ complex; tetrabutyl ammonium fluoride; hydrogen; sodium acetate; silica gel; triethylamine; N-ethyl-N,N-diisopropylamine; HATU; trifluoroacetic acid; sodium iodide; dmap; cerium(III) chloride heptahydrate; palladium 10% on activated carbon; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; ethanol; dichloromethane; dimethyl sulfoxide; acetonitrile;

Reference yield:

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

: 1218929-58-8
(3aR,6aR)-4-(2-tert-butoxycarbonylamino-(2S)-cyclohexyl-acetyl)-(3S)-(1H-indol-3-yl)-hexahydro-pyrrolo[3,2-b]pyrrole-1-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 9 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

8.1: trifluoroacetic acid / dichloromethane / 2 h / 0 °C

9.1: N-ethyl-N,N-diisopropylamine; HATU / 1-methyl-pyrrolidin-2-one / 0 - 20 °C

With tetrabutyl ammonium fluoride; hydrogen; sodium acetate; silica gel; triethylamine; N-ethyl-N,N-diisopropylamine; HATU; trifluoroacetic acid; sodium iodide; dmap; cerium(III) chloride heptahydrate; palladium 10% on activated carbon; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; ethanol; dichloromethane; acetonitrile;