Dithiocarbonic acid O-{(R)-3-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3-ethyl-1-[2-(1H-indol-3-yl)-ethyl]-2-oxo-piperidin-4-yl} ester S-methyl ester

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Chemical Name:Dithiocarbonic acid O-{(R)-3-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3-ethyl-1-[2-(1H-indol-3-yl)-ethyl]-2-oxo-piperidin-4-yl} ester S-methyl ester
CAS No.:190378-34-8
Molecular Formula:C₃₈H₄₈N₂O₃S₂Si
Molecular Weight:673.028
Hs Code.:

Synonyms:Dithiocarbonic acid O-{(R)-3-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3-ethyl-1-[2-(1H-indol-3-yl)-ethyl]-2-oxo-piperidin-4-yl} ester S-methyl ester

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Chemical Property of Dithiocarbonic acid O-{(R)-3-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3-ethyl-1-[2-(1H-indol-3-yl)-ethyl]-2-oxo-piperidin-4-yl} ester S-methyl ester

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Technology Process of Dithiocarbonic acid O-{(R)-3-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3-ethyl-1-[2-(1H-indol-3-yl)-ethyl]-2-oxo-piperidin-4-yl} ester S-methyl ester

There total 10 articles about Dithiocarbonic acid O-{(R)-3-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3-ethyl-1-[2-(1H-indol-3-yl)-ethyl]-2-oxo-piperidin-4-yl} ester S-methyl 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:

: 61-54-1
tryptamine

: 190378-34-8
Dithiocarbonic acid O-{(R)-3-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3-ethyl-1-[2-(1H-indol-3-yl)-ethyl]-2-oxo-piperidin-4-yl} ester S-methyl ester

Guidance literature:: Multi-step reaction with 10 steps

1: 83 percent / tetrahydrofuran / 12 h / 20 °C

2: 83 percent / 1,4-bis(methylamino)pyridine, DCC / CH₂Cl₂ / 18 h / 20 °C

3: 79 percent / NaH / tetrahydrofuran / 4 h / 20 °C

4: 79 percent / LiBr, H₂O / dimethylformamide / 12 h / Heating

5: p-TsOH / toluene / 12 h / Heating

6: 1.) hydroquinone, 2.) 20percent AcOH / 1.) THF, 60 deg C, 2 d,2.) H₂O, THF, 40 deg C, 72 h

7: 76 percent / LiOH, 30percent H₂O₂ / methanol / 5 h / 20 °C

8: 1.) Et₃N, isobutyl chloroformate, 2.) NaBH₄ / 1.) THF, 0 deg C, 30 min, 2.) CH₃OH, 20 deg C, 3 h

9: 68 percent / imidazole / dimethylformamide / 12 h / 20 °C

10: 1.) NaH, imidazole / 1.) THF, 20 deg C, 30 min, 2.) 30 min, 3.) 15 min

With 1H-imidazole; lithium hydroxide; sodium tetrahydroborate; 1,4-bis(methylamino)pyridine; water; dihydrogen peroxide; sodium hydride; toluene-4-sulfonic acid; acetic acid; triethylamine; hydroquinone; dicyclohexyl-carbodiimide; lithium bromide; isobutyl chloroformate; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo9622690

Reference yield:

: 14487-98-0
3-<<2-(1H-indol-3-yl)ethyl>amino>propanoic acid ethyl ester

: 190378-34-8
Dithiocarbonic acid O-{(R)-3-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3-ethyl-1-[2-(1H-indol-3-yl)-ethyl]-2-oxo-piperidin-4-yl} ester S-methyl ester

Guidance literature:: Multi-step reaction with 9 steps

1: 83 percent / 1,4-bis(methylamino)pyridine, DCC / CH₂Cl₂ / 18 h / 20 °C

2: 79 percent / NaH / tetrahydrofuran / 4 h / 20 °C

3: 79 percent / LiBr, H₂O / dimethylformamide / 12 h / Heating

4: p-TsOH / toluene / 12 h / Heating

5: 1.) hydroquinone, 2.) 20percent AcOH / 1.) THF, 60 deg C, 2 d,2.) H₂O, THF, 40 deg C, 72 h

6: 76 percent / LiOH, 30percent H₂O₂ / methanol / 5 h / 20 °C

7: 1.) Et₃N, isobutyl chloroformate, 2.) NaBH₄ / 1.) THF, 0 deg C, 30 min, 2.) CH₃OH, 20 deg C, 3 h

8: 68 percent / imidazole / dimethylformamide / 12 h / 20 °C

9: 1.) NaH, imidazole / 1.) THF, 20 deg C, 30 min, 2.) 30 min, 3.) 15 min

With 1H-imidazole; lithium hydroxide; sodium tetrahydroborate; 1,4-bis(methylamino)pyridine; water; dihydrogen peroxide; sodium hydride; toluene-4-sulfonic acid; acetic acid; triethylamine; hydroquinone; dicyclohexyl-carbodiimide; lithium bromide; isobutyl chloroformate; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo9622690

Reference yield:

: 190378-04-2
3-ethyl-1-[2-(1H-indol-3-yl)ethyl]-2,4-piperidinedione

: 190378-34-8
Dithiocarbonic acid O-{(R)-3-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3-ethyl-1-[2-(1H-indol-3-yl)-ethyl]-2-oxo-piperidin-4-yl} ester S-methyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: p-TsOH / toluene / 12 h / Heating

2: 1.) hydroquinone, 2.) 20percent AcOH / 1.) THF, 60 deg C, 2 d,2.) H₂O, THF, 40 deg C, 72 h

3: 76 percent / LiOH, 30percent H₂O₂ / methanol / 5 h / 20 °C

4: 1.) Et₃N, isobutyl chloroformate, 2.) NaBH₄ / 1.) THF, 0 deg C, 30 min, 2.) CH₃OH, 20 deg C, 3 h

5: 68 percent / imidazole / dimethylformamide / 12 h / 20 °C

6: 1.) NaH, imidazole / 1.) THF, 20 deg C, 30 min, 2.) 30 min, 3.) 15 min

With 1H-imidazole; lithium hydroxide; sodium tetrahydroborate; dihydrogen peroxide; sodium hydride; toluene-4-sulfonic acid; acetic acid; triethylamine; hydroquinone; isobutyl chloroformate; In methanol; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo9622690