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

Base Information

Chemical Name:4-benzyloxy-2-(5-imidazol-1-yl-1H-indol-3-ylmethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester
CAS No.:250122-43-1
Molecular Formula:C₂₈H₃₂N₄O₃
Molecular Weight:472.587
Hs Code.:

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

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

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

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

There total 10 articles about 4-benzyloxy-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: 77.0%

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

: 250122-42-0
3-((2S,4R)-4-Benzyloxy-pyrrolidin-2-ylmethyl)-5-imidazol-1-yl-1H-indole

: 250122-43-1
4-benzyloxy-2-(5-imidazol-1-yl-1H-indol-3-ylmethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:: In tetrahydrofuran; at 20 ℃; for 4h;
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

: 250122-43-1
4-benzyloxy-2-(5-imidazol-1-yl-1H-indol-3-ylmethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 8 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

With sulfuric acid; hydrogen; potassium hexamethylsilazane; sodium hydride; diisobutylaluminium hydride; triethylamine; platinum(IV) oxide; In tetrahydrofuran; dichloromethane; 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;
DOI:10.1016/S0960-894X(99)00409-6

Reference yield:

: 114676-69-6
(2R,4R)-1-tert-butyl 2-methyl 4-hydroxypyrrolidine-1,2-dicarboxylate

: 250122-43-1
4-benzyloxy-2-(5-imidazol-1-yl-1H-indol-3-ylmethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 7 steps

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

2: 39 percent / DIBALH / toluene / 2.25 h / -78 °C

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

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

5: DIBALH / toluene / 2 h / -81 °C

6: 24 percent / 4 percent aq. H₂SO₄ / 20 h / Heating

7: 77 percent / tetrahydrofuran / 4 h / 20 °C

With sulfuric acid; hydrogen; potassium hexamethylsilazane; sodium hydride; diisobutylaluminium hydride; platinum(IV) oxide; In tetrahydrofuran; ethyl acetate; N,N-dimethyl-formamide; toluene; 1: Etherification / 2: Reduction / 3: Wittig's reaction / 4: Catalytic hydrogenation / 5: Reduction / 6: Fischer indolisation; deprotection / 7: Substitution;
DOI:10.1016/S0960-894X(99)00409-6