4-(benzylamino-methyl)-2-(5-imidazol-1-yl-1H-indol-3-ylmethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Base Information

Chemical Name:4-(benzylamino-methyl)-2-(5-imidazol-1-yl-1H-indol-3-ylmethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester
CAS No.:250122-46-4
Molecular Formula:C₂₉H₃₅N₅O₂
Molecular Weight:485.629
Hs Code.:

4-(benzylamino-methyl)-2-(5-imidazol-1-yl-1<i>H</i>-indol-3-ylmethyl)-pyrrolidine-1-carboxylic acid <i>tert</i>-butyl ester

Synonyms:4-(benzylamino-methyl)-2-(5-imidazol-1-yl-1H-indol-3-ylmethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

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Chemical Property of 4-(benzylamino-methyl)-2-(5-imidazol-1-yl-1H-indol-3-ylmethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

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Technology Process of 4-(benzylamino-methyl)-2-(5-imidazol-1-yl-1H-indol-3-ylmethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

There total 15 articles about 4-(benzylamino-methyl)-2-(5-imidazol-1-yl-1H-indol-3-ylmethyl)-pyrrolidine-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: 79.0%

: 100-52-7
benzaldehyde

: 250122-45-3
4-aminomethyl-2-(5-imidazol-1-yl-1H-indol-3-ylmethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

: 250122-46-4
4-(benzylamino-methyl)-2-(5-imidazol-1-yl-1H-indol-3-ylmethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:: With sodium cyanoborohydride; acetic acid; In methanol; at 20 ℃; for 1.75h;
DOI:10.1016/S0960-894X(99)00409-6

Reference yield:

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

: 250122-46-4
4-(benzylamino-methyl)-2-(5-imidazol-1-yl-1H-indol-3-ylmethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 77 percent / tetrahydrofuran / 4 h / 20 °C

2: 88 percent / HCO₂NH₄ / 10 percent Pd/C / methanol / 6 h / 55 - 62 °C

3: Et₃N / tetrahydrofuran / 2 h / 20 °C

4: dimethylformamide / 12 h / 65 °C

5: H₂ / PtO₂ / CHCl₃; ethanol / 17 h / 2585.74 Torr

6: 79 percent / NaCNBH₃; AcOH / methanol / 1.75 h / 20 °C

With hydrogen; ammonium formate; sodium cyanoborohydride; acetic acid; triethylamine; platinum(IV) oxide; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; chloroform; N,N-dimethyl-formamide; 1: Substitution / 2: debenzylation / 3: Esterification / 4: Substitution / 5: Catalytic hydrogenation / 6: reductive benzylation;
DOI:10.1016/S0960-894X(99)00409-6

Reference yield:

: 114676-47-0,775275-31-5,790644-51-8,754962-86-2
(2R,4R)-4-Hydroxy-pyrrolidine-2-carboxylic acid methyl ester

: 250122-46-4
4-(benzylamino-methyl)-2-(5-imidazol-1-yl-1H-indol-3-ylmethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 13 steps

1: Et₃N / CH₂Cl₂ / 3 h / 20 °C

2: NaH / dimethylformamide / 4 h / 5 °C

3: 39 percent / DIBALH / toluene / 2.25 h / -78 °C

4: KHMDS / tetrahydrofuran / 3 h / -78 - 20 °C

5: H₂ / PtO₂ / ethyl acetate / 0.67 h / 620.58 Torr

6: DIBALH / toluene / 2 h / -81 °C

7: 24 percent / 4 percent aq. H₂SO₄ / 20 h / Heating

8: 77 percent / tetrahydrofuran / 4 h / 20 °C

9: 88 percent / HCO₂NH₄ / 10 percent Pd/C / methanol / 6 h / 55 - 62 °C

10: Et₃N / tetrahydrofuran / 2 h / 20 °C

11: dimethylformamide / 12 h / 65 °C

12: H₂ / PtO₂ / CHCl₃; ethanol / 17 h / 2585.74 Torr

13: 79 percent / NaCNBH₃; AcOH / methanol / 1.75 h / 20 °C

With sulfuric acid; hydrogen; ammonium formate; potassium hexamethylsilazane; sodium hydride; diisobutylaluminium hydride; sodium cyanoborohydride; acetic acid; triethylamine; platinum(IV) oxide; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; chloroform; ethyl acetate; N,N-dimethyl-formamide; toluene; 1: Substitution / 2: Etherification / 3: Reduction / 4: Wittig's reaction / 5: Catalytic hydrogenation / 6: Reduction / 7: Fischer indolisation; deprotection / 8: Substitution / 9: debenzylation / 10: Esterification / 11: Substitution / 12: Catalytic hydrogenation / 13: reductive benzylation;
DOI:10.1016/S0960-894X(99)00409-6