(1S,12bR)-1-ethyl-1-(2-tert-butyldiphenylsilyloxyethyl)-4-oxo-2,3,6,7,12,12b-hexahydro-1H-indolo[2,3-a]quinolizine

Base Information

• Chemical Name: (1S,12bR)-1-ethyl-1-(2-tert-butyldiphenylsilyloxyethyl)-4-oxo-2,3,6,7,12,12b-hexahydro-1H-indolo[2,3-a]quinolizine
• CAS No.: 393563-22-9
• Molecular Formula: C₃₅H₄₂N₂O₂Si
• Molecular Weight: 550.816
• Mol file: 393563-22-9.mol

Synonyms:(1S,12bR)-1-ethyl-1-(2-tert-butyldiphenylsilyloxyethyl)-4-oxo-2,3,6,7,12,12b-hexahydro-1H-indolo[2,3-a]quinolizine

Chemical Property of (1S,12bR)-1-ethyl-1-(2-tert-butyldiphenylsilyloxyethyl)-4-oxo-2,3,6,7,12,12b-hexahydro-1H-indolo[2,3-a]quinolizine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,12bR)-1-ethyl-1-(2-tert-butyldiphenylsilyloxyethyl)-4-oxo-2,3,6,7,12,12b-hexahydro-1H-indolo[2,3-a]quinolizine

There total 19 articles about (1S,12bR)-1-ethyl-1-(2-tert-butyldiphenylsilyloxyethyl)-4-oxo-2,3,6,7,12,12b-hexahydro-1H-indolo[2,3-a]quinolizine 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: 95.0%

(4S)-N-[2-(3-indolyl)ethyl]-4-ethyl-4-(2-tert-butyldiphenylsiloxyethyl)-5-oxopentamide (393563-17-2) → (1S,12bS)-1-ethyl-1-(2-tert-butyldiphenylsilyloxyethyl)-4-oxo-2,3,6,7,12,12b-hexahydro-1H-indolo[2,3-a]quinolizine (393563-18-3) + (1S,12bR)-1-ethyl-1-(2-tert-butyldiphenylsilyloxyethyl)-4-oxo-2,3,6,7,12,12b-hexahydro-1H-indolo[2,3-a]quinolizine (393563-22-9)

Guidance literature:

With Nafion-H; In toluene; at 20 ℃; for 18h;

DOI:10.1016/S0040-4039(99)02131-0

Reference yield: 95.0%

(5S)-N-[2-(3-indolyl)ethyl]-5-ethyl-5-(2-tert-butyldiphenylsiloxyethyl)-6-hydroxy-δ-lactam (262847-04-1) → (1S,12bS)-1-ethyl-1-(2-tert-butyldiphenylsilyloxyethyl)-4-oxo-2,3,6,7,12,12b-hexahydro-1H-indolo[2,3-a]quinolizine (393563-18-3) + (1S,12bR)-1-ethyl-1-(2-tert-butyldiphenylsilyloxyethyl)-4-oxo-2,3,6,7,12,12b-hexahydro-1H-indolo[2,3-a]quinolizine (393563-22-9)

Guidance literature:

With Nafion-H; In toluene; at 20 ℃; for 18h;

DOI:10.1016/S0040-4039(99)02131-0

Reference yield:

(4R,5S)-3-[(2S)-1-oxo-2-ethyl-4-pentenyl]-4-methyl-5-phenyl-2-oxazolidinone (121074-25-7,121074-20-2) → (1S,12bR)-1-ethyl-1-(2-tert-butyldiphenylsilyloxyethyl)-4-oxo-2,3,6,7,12,12b-hexahydro-1H-indolo[2,3-a]quinolizine (393563-22-9)

Guidance literature:

Multi-step reaction with 13 steps

1.1: 50 percent / LiAlH₄ / -5 °C

2.1: 86 percent / DCC; DMAP / CH₂Cl₂ / 1 h / 0 °C

3.1: disiamylborane / tetrahydrofuran / 0 - 20 °C

3.2: 74 percent / H₂O₂; NaOH / tetrahydrofuran; H₂O / 0.33 h / 10 - 20 °C

4.1: 89 percent / pyridine / 12 h / 0 - 20 °C

5.1: 88 percent / MsN₃; Et₃N / acetonitrile / 10 h / 20 °C

6.1: 87 percent / Rh₂(OAc)4 / CH₂Cl₂ / 14 h / Heating

7.1: 84 percent / NaCl; H₂O / dimethylsulfoxide / 12 h / 110 °C

8.1: 93 percent / Bu₄NF / tetrahydrofuran / 0.67 h / 20 °C

9.1: 98 percent / Jones reagent / acetone / 0 °C

10.1: DCC / CH₂Cl₂ / 1 h / 0 °C

10.2: 67 percent / CH₂Cl₂ / 15 h / 20 °C

11.1: 92 percent / LiBH₄ / tetrahydrofuran; methanol / 48 h / 20 °C

12.1: 92 percent / imidazole / dimethylformamide / 16 h / -20 - 20 °C

13.1: Et₃N; Py*SO₃ / dimethylsulfoxide / 60 h / 20 °C

13.2: 49.4 mg / TFA / CH₂Cl₂ / 16 h / -42 - 20 °C

With pyridine; 1H-imidazole; dmap; lithium aluminium tetrahydride; lithium borohydride; jones reagent; tetrabutyl ammonium fluoride; water; sulfur trioxide pyridine complex; bis-(1,2-dimethylpropyl)borane; triethylamine; Methanesulfonyl azide; dicyclohexyl-carbodiimide; sodium chloride; dirhodium tetraacetate; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; acetonitrile; 9.1: Jones oxidation / 13.2: Pictet-Spengler cyclization;

DOI:10.1021/jo010751z

upstream raw materials:

(4S)-N-[2-(3-indolyl)ethyl]-4-ethyl-4-(2-tert-butyldiphenylsiloxyethyl)-5-oxopentamide

(5S)-N-[2-(3-indolyl)ethyl]-5-ethyl-5-(2-tert-butyldiphenylsiloxyethyl)-6-hydroxy-δ-lactam

(4R,5S)-3-[(2S)-1-oxo-2-ethyl-4-pentenyl]-4-methyl-5-phenyl-2-oxazolidinone

(4S)-N-[2-(indol-3-yl)-ethyl]-4-ethyl-4-hydroxymethyl-6-hydroxyhexamide

Downstream raw materials:

vinburnine