tert-butyl 5-[2-(7-azabicyclo[2.2.1]hept-7-yl)-1,1-dimethyl-2-oxoethyl]-3-[(1S)-2-(benzyloxy)-1-methylethyl]-2-(3,4,5-trimethylphenyl)-1H-indole-1-carboxylate

Base Information

Chemical Name:tert-butyl 5-[2-(7-azabicyclo[2.2.1]hept-7-yl)-1,1-dimethyl-2-oxoethyl]-3-[(1S)-2-(benzyloxy)-1-methylethyl]-2-(3,4,5-trimethylphenyl)-1H-indole-1-carboxylate
CAS No.:357193-15-8
Molecular Formula:C₄₂H₅₂N₂O₄
Molecular Weight:648.886
Hs Code.:

tert-butyl 5-[2-(7-azabicyclo[2.2.1]hept-7-yl)-1,1-dimethyl-2-oxoethyl]-3-[(1S)-2-(benzyloxy)-1-methylethyl]-2-(3,4,5-trimethylphenyl)-1H-indole-1-carboxylate

Synonyms:tert-butyl 5-[2-(7-azabicyclo[2.2.1]hept-7-yl)-1,1-dimethyl-2-oxoethyl]-3-[(1S)-2-(benzyloxy)-1-methylethyl]-2-(3,4,5-trimethylphenyl)-1H-indole-1-carboxylate

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Chemical Property of tert-butyl 5-[2-(7-azabicyclo[2.2.1]hept-7-yl)-1,1-dimethyl-2-oxoethyl]-3-[(1S)-2-(benzyloxy)-1-methylethyl]-2-(3,4,5-trimethylphenyl)-1H-indole-1-carboxylate

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Technology Process of tert-butyl 5-[2-(7-azabicyclo[2.2.1]hept-7-yl)-1,1-dimethyl-2-oxoethyl]-3-[(1S)-2-(benzyloxy)-1-methylethyl]-2-(3,4,5-trimethylphenyl)-1H-indole-1-carboxylate

There total 15 articles about tert-butyl 5-[2-(7-azabicyclo[2.2.1]hept-7-yl)-1,1-dimethyl-2-oxoethyl]-3-[(1S)-2-(benzyloxy)-1-methylethyl]-2-(3,4,5-trimethylphenyl)-1H-indole-1-carboxylate 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:

: 83397-45-9
ethyl 2-methyl-2-(4-nitrophenyl)propanoate

: 357193-15-8
tert-butyl 5-[2-(7-azabicyclo[2.2.1]hept-7-yl)-1,1-dimethyl-2-oxoethyl]-3-[(1S)-2-(benzyloxy)-1-methylethyl]-2-(3,4,5-trimethylphenyl)-1H-indole-1-carboxylate

Guidance literature:: Multi-step reaction with 8 steps

1.1: 97 percent / NaOH / methanol / 4 h / 60 °C

2.1: (COCl)2; DMF / toluene / 80 °C

2.2: 96 percent / Et₃N / CH₂Cl₂ / 12 h / 20 °C

3.1: 100 percent / H₂ / 10 percent Pd/C / ethanol / 1 h / 20 °C / 2327.17 Torr

4.1: 97 percent / CaCO₃; ICl / methanol; H₂O / 0.5 h / 20 °C

5.1: 72 percent / K₂CO₃; LiCl; PPh₃ / Pd(OAc)2 / dimethylformamide / 16 h / 100 °C

6.1: 92 percent / AgBF₄; ICl / methanol; tetrahydrofuran / 0.25 h / 0 °C

7.1: 96 percent / 2M Na₂CO₃ / (dppf)PdCl₂*CH₂Cl₂ / toluene; ethanol / 15 h / 80 °C

8.1: DMAP / CH₂Cl₂ / 2 h / 20 °C

With dmap; sodium hydroxide; silver tetrafluoroborate; oxalyl dichloride; hydrogen; Iodine monochloride; sodium carbonate; potassium carbonate; N,N-dimethyl-formamide; triphenylphosphine; calcium carbonate; lithium chloride; palladium diacetate; palladium on activated charcoal; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; 5.1: Larock reaction;
DOI:10.1016/S0040-4020(01)00367-2

Reference yield:

: 81927-55-1
O-benzyl 2,2,2-trichloroacetimidate

: 357193-15-8
tert-butyl 5-[2-(7-azabicyclo[2.2.1]hept-7-yl)-1,1-dimethyl-2-oxoethyl]-3-[(1S)-2-(benzyloxy)-1-methylethyl]-2-(3,4,5-trimethylphenyl)-1H-indole-1-carboxylate

Guidance literature:: Multi-step reaction with 9 steps

1.1: 74 percent / CF₃SO₃H / cyclohexane; CCl₄ / 16 h / 20 °C

2.1: 89 percent / LiAlH₄ / tetrahydrofuran / 4 h / 20 °C

3.1: oxalyl chloride; DMSO; i-Pr₂NEt / CH₂Cl₂ / -78 - -15 °C

4.1: 46.54 g / PPh₃ / CH₂Cl₂ / 0 - 20 °C

5.1: n-BuLi / tetrahydrofuran; hexane / 2 h / -78 - 20 °C

5.2: 94 percent / tetrahydrofuran; hexane / 1 h / 0 - 10 °C

6.1: 72 percent / K₂CO₃; LiCl; PPh₃ / Pd(OAc)2 / dimethylformamide / 16 h / 100 °C

7.1: 92 percent / AgBF₄; ICl / methanol; tetrahydrofuran / 0.25 h / 0 °C

8.1: 96 percent / 2M Na₂CO₃ / (dppf)PdCl₂*CH₂Cl₂ / toluene; ethanol / 15 h / 80 °C

9.1: DMAP / CH₂Cl₂ / 2 h / 20 °C

With dmap; lithium aluminium tetrahydride; silver tetrafluoroborate; n-butyllithium; oxalyl dichloride; trifluorormethanesulfonic acid; Iodine monochloride; sodium carbonate; potassium carbonate; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; triphenylphosphine; lithium chloride; palladium diacetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In tetrahydrofuran; methanol; tetrachloromethane; ethanol; hexane; dichloromethane; cyclohexane; N,N-dimethyl-formamide; toluene; 3.1: Swern-Moffat oxidation / 6.1: Larock reaction;
DOI:10.1016/S0040-4020(01)00367-2

Reference yield:

: 63930-46-1
(S)-3-benzyloxy-2-methylpropan-1-ol

: 357193-15-8
tert-butyl 5-[2-(7-azabicyclo[2.2.1]hept-7-yl)-1,1-dimethyl-2-oxoethyl]-3-[(1S)-2-(benzyloxy)-1-methylethyl]-2-(3,4,5-trimethylphenyl)-1H-indole-1-carboxylate

Guidance literature:: Multi-step reaction with 7 steps

1.1: oxalyl chloride; DMSO; i-Pr₂NEt / CH₂Cl₂ / -78 - -15 °C

2.1: 46.54 g / PPh₃ / CH₂Cl₂ / 0 - 20 °C

3.1: n-BuLi / tetrahydrofuran; hexane / 2 h / -78 - 20 °C

3.2: 94 percent / tetrahydrofuran; hexane / 1 h / 0 - 10 °C

4.1: 72 percent / K₂CO₃; LiCl; PPh₃ / Pd(OAc)2 / dimethylformamide / 16 h / 100 °C

5.1: 92 percent / AgBF₄; ICl / methanol; tetrahydrofuran / 0.25 h / 0 °C

6.1: 96 percent / 2M Na₂CO₃ / (dppf)PdCl₂*CH₂Cl₂ / toluene; ethanol / 15 h / 80 °C

7.1: DMAP / CH₂Cl₂ / 2 h / 20 °C

With dmap; silver tetrafluoroborate; n-butyllithium; oxalyl dichloride; Iodine monochloride; sodium carbonate; potassium carbonate; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; triphenylphosphine; lithium chloride; palladium diacetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; 1.1: Swern-Moffat oxidation / 4.1: Larock reaction;
DOI:10.1016/S0040-4020(01)00367-2