tert-butyl [2-(2-benzenesulfinyl-1H-indol-3-yl)-ethyl]-[1-(t-butyldimethylsilanyloxy)-2-phenyl-vinyl]carbamate

Base Information

Chemical Name:tert-butyl [2-(2-benzenesulfinyl-1H-indol-3-yl)-ethyl]-[1-(t-butyldimethylsilanyloxy)-2-phenyl-vinyl]carbamate
CAS No.:712273-27-3
Molecular Formula:C₃₅H₄₄N₂O₄SSi
Molecular Weight:616.897
Hs Code.:

Synonyms:tert-butyl [2-(2-benzenesulfinyl-1H-indol-3-yl)-ethyl]-[1-(t-butyldimethylsilanyloxy)-2-phenyl-vinyl]carbamate

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Chemical Property of tert-butyl [2-(2-benzenesulfinyl-1H-indol-3-yl)-ethyl]-[1-(t-butyldimethylsilanyloxy)-2-phenyl-vinyl]carbamate

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Technology Process of tert-butyl [2-(2-benzenesulfinyl-1H-indol-3-yl)-ethyl]-[1-(t-butyldimethylsilanyloxy)-2-phenyl-vinyl]carbamate

There total 8 articles about tert-butyl [2-(2-benzenesulfinyl-1H-indol-3-yl)-ethyl]-[1-(t-butyldimethylsilanyloxy)-2-phenyl-vinyl]carbamate 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: 38.0%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 712273-37-5
[2-(2-benzylsulfinyl-1H-indol-3-yl)-ethyl]phenylacetylcarbamate

: 712273-27-3
tert-butyl [2-(2-benzenesulfinyl-1H-indol-3-yl)-ethyl]-[1-(t-butyldimethylsilanyloxy)-2-phenyl-vinyl]carbamate

Guidance literature:: With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; lithium hexamethyldisilazane; In tetrahydrofuran; at -75 - 20 ℃; for 3h;
DOI:10.1021/jo050896w

Reference yield:

: 61-54-1
tryptamine

: 712273-27-3
tert-butyl [2-(2-benzenesulfinyl-1H-indol-3-yl)-ethyl]-[1-(t-butyldimethylsilanyloxy)-2-phenyl-vinyl]carbamate

Guidance literature:: Multi-step reaction with 7 steps

1: 80 percent / ethyldiisopropylamine / tetrahydrofuran / 0.5 h

2: 84 percent / hydrochloric acid / dioxane / 0.08 h

3: 69 percent / NaH; 4-(dimethylamino)pyridine / tetrahydrofuran / 5 h

4: 90 percent / lithium hexamethyldisilazide; 4-(dimethylamino)pyridine / tetrahydrofuran / 2 h / 20 °C

5: 100 percent / hydrogen / Pd(OH)2/C / tetrahydrofuran / 1 h / 20 °C

6: 94 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 0.5 h / -5 °C

7: 38 percent / lithium hexamethyldisilazide; DMPU / tetrahydrofuran / 3 h / -75 - 20 °C

With hydrogenchloride; dmap; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; hydrogen; sodium hydride; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; lithium hexamethyldisilazane; palladium dihydroxide; In tetrahydrofuran; 1,4-dioxane; dichloromethane;
DOI:10.1021/jo050896w

Reference yield:

: 19462-24-9
N-phenylacetyltryptamine

: 712273-27-3
tert-butyl [2-(2-benzenesulfinyl-1H-indol-3-yl)-ethyl]-[1-(t-butyldimethylsilanyloxy)-2-phenyl-vinyl]carbamate

Guidance literature:: Multi-step reaction with 6 steps

1: 84 percent / hydrochloric acid / dioxane / 0.08 h

2: 69 percent / NaH; 4-(dimethylamino)pyridine / tetrahydrofuran / 5 h

3: 90 percent / lithium hexamethyldisilazide; 4-(dimethylamino)pyridine / tetrahydrofuran / 2 h / 20 °C

4: 100 percent / hydrogen / Pd(OH)2/C / tetrahydrofuran / 1 h / 20 °C

5: 94 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 0.5 h / -5 °C

6: 38 percent / lithium hexamethyldisilazide; DMPU / tetrahydrofuran / 3 h / -75 - 20 °C

With hydrogenchloride; dmap; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; hydrogen; sodium hydride; 3-chloro-benzenecarboperoxoic acid; lithium hexamethyldisilazane; palladium dihydroxide; In tetrahydrofuran; 1,4-dioxane; dichloromethane;
DOI:10.1021/jo050896w