3-(2-benzyloxycarbonylamino-2-methoxycarbonyl-ethyl)-7,7-dimethyl-7H-pyrano[2,3-g]indole-1-carboxylic acid tert-butyl ester

Base Information

Chemical Name:3-(2-benzyloxycarbonylamino-2-methoxycarbonyl-ethyl)-7,7-dimethyl-7H-pyrano[2,3-g]indole-1-carboxylic acid tert-butyl ester
CAS No.:905981-24-0
Molecular Formula:C₃₀H₃₄N₂O₇
Molecular Weight:534.609
Hs Code.:

3-(2-benzyloxycarbonylamino-2-methoxycarbonyl-ethyl)-7,7-dimethyl-7<i>H</i>-pyrano[2,3-<i>g</i>]indole-1-carboxylic acid <i>tert</i>-butyl ester

Synonyms:3-(2-benzyloxycarbonylamino-2-methoxycarbonyl-ethyl)-7,7-dimethyl-7H-pyrano[2,3-g]indole-1-carboxylic acid tert-butyl ester

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Chemical Property of 3-(2-benzyloxycarbonylamino-2-methoxycarbonyl-ethyl)-7,7-dimethyl-7H-pyrano[2,3-g]indole-1-carboxylic acid tert-butyl ester

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Technology Process of 3-(2-benzyloxycarbonylamino-2-methoxycarbonyl-ethyl)-7,7-dimethyl-7H-pyrano[2,3-g]indole-1-carboxylic acid tert-butyl ester

There total 9 articles about 3-(2-benzyloxycarbonylamino-2-methoxycarbonyl-ethyl)-7,7-dimethyl-7H-pyrano[2,3-g]indole-1-carboxylic acid 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: 77.0%

: 848467-52-7
2-benzyloxycarbonylamino-3-(7,7-dimethyl-1,7-dihydro-pyrano[2,3-g]indol-3-yl)-propionic acid methyl ester

: 24424-99-5
di-tert-butyl dicarbonate

: 905981-24-0
3-(2-benzyloxycarbonylamino-2-methoxycarbonyl-ethyl)-7,7-dimethyl-7H-pyrano[2,3-g]indole-1-carboxylic acid tert-butyl ester

Guidance literature:: With dmap; In dichloromethane; acetonitrile; at 25 ℃; for 0.5h;
DOI:10.1002/anie.200461864

Reference yield:

: 5-oxo-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

: 905981-24-0
3-(2-benzyloxycarbonylamino-2-methoxycarbonyl-ethyl)-7,7-dimethyl-7H-pyrano[2,3-g]indole-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: lithium triethylborohydride / tetrahydrofuran / 0.17 h / -78 °C

2: 75 percent / diazabicyclo[2.2.2]octane; tetrabutylammonium iodide / Pd(OAc)2 / dimethylformamide / 4 h / 85 °C

3: 95 percent / 4-(dimethylamino)pyridine / CH₂Cl₂; acetonitrile / 0.5 h / 25 °C

4: Mg / methanol / 2.5 h / 0 - 25 °C

5: 2.81 g / CuCl₂; 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 24 h / 0 °C

6: 1.51 g / acetic acid / 1.33 h / 120 °C

7: 77 percent / 4-(dimethylamino)pyridine / CH₂Cl₂; acetonitrile / 0.5 h / 25 °C

With 1,4-diaza-bicyclo[2.2.2]octane; dmap; tetra-(n-butyl)ammonium iodide; lithium triethylborohydride; magnesium; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; copper dichloride; palladium diacetate; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1002/anie.200461864

Reference yield:

: 93271-97-7
1-benzyloxycarbonyl-5-hydroxy-2-methoxycarbonylpyrrolidine

: 905981-24-0
3-(2-benzyloxycarbonylamino-2-methoxycarbonyl-ethyl)-7,7-dimethyl-7H-pyrano[2,3-g]indole-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 75 percent / diazabicyclo[2.2.2]octane; tetrabutylammonium iodide / Pd(OAc)2 / dimethylformamide / 4 h / 85 °C

2: 95 percent / 4-(dimethylamino)pyridine / CH₂Cl₂; acetonitrile / 0.5 h / 25 °C

3: Mg / methanol / 2.5 h / 0 - 25 °C

4: 2.81 g / CuCl₂; 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 24 h / 0 °C

5: 1.51 g / acetic acid / 1.33 h / 120 °C

6: 77 percent / 4-(dimethylamino)pyridine / CH₂Cl₂; acetonitrile / 0.5 h / 25 °C

With 1,4-diaza-bicyclo[2.2.2]octane; dmap; tetra-(n-butyl)ammonium iodide; magnesium; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; copper dichloride; palladium diacetate; In methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1002/anie.200461864