(1R,2S,6R)-N-benzyl-N-methyl-2-((1-methyl-1H-indol-3-yl)methyl)-3-(phenylsulfonyl)-3-azabicyclo[4.1.0]heptan-1-amine

Base Information

Chemical Name:(1R,2S,6R)-N-benzyl-N-methyl-2-((1-methyl-1H-indol-3-yl)methyl)-3-(phenylsulfonyl)-3-azabicyclo[4.1.0]heptan-1-amine
CAS No.:1266347-65-2
Molecular Formula:C₃₀H₃₃N₃O₂S
Molecular Weight:499.677
Hs Code.:

Synonyms:(1R,2S,6R)-N-benzyl-N-methyl-2-((1-methyl-1H-indol-3-yl)methyl)-3-(phenylsulfonyl)-3-azabicyclo[4.1.0]heptan-1-amine

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Chemical Property of (1R,2S,6R)-N-benzyl-N-methyl-2-((1-methyl-1H-indol-3-yl)methyl)-3-(phenylsulfonyl)-3-azabicyclo[4.1.0]heptan-1-amine

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Technology Process of (1R,2S,6R)-N-benzyl-N-methyl-2-((1-methyl-1H-indol-3-yl)methyl)-3-(phenylsulfonyl)-3-azabicyclo[4.1.0]heptan-1-amine

There total 6 articles about (1R,2S,6R)-N-benzyl-N-methyl-2-((1-methyl-1H-indol-3-yl)methyl)-3-(phenylsulfonyl)-3-azabicyclo[4.1.0]heptan-1-amine 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: 69.0%

: 1266347-57-2
(S)-N-benzyl-2-(N-(but-3-en-1-yl)phenylsulfonamido)-N-methyl-3-(1-methyl-1H-indol-3-yl)propanamide

: 1266347-65-2
(1R,2S,6R)-N-benzyl-N-methyl-2-((1-methyl-1H-indol-3-yl)methyl)-3-(phenylsulfonyl)-3-azabicyclo[4.1.0]heptan-1-amine

Guidance literature:: (S)-N-benzyl-2-(N-(but-3-en-1-yl)phenylsulfonamido)-N-methyl-3-(1-methyl-1H-indol-3-yl)propanamide; With triisopropoxytitanium(IV) chloride; In tetrahydrofuran; Inert atmosphere;

With cyclohexylmagnesiumchloride; In tetrahydrofuran; for 13h; Inert atmosphere;
DOI:10.1021/ol103105q

Reference yield:

: (2S)-2-amino-3-(1-methyl-1H-indol-3-yl)propionic acid methyl ester hydrochloride

: 1266347-65-2
(1R,2S,6R)-N-benzyl-N-methyl-2-((1-methyl-1H-indol-3-yl)methyl)-3-(phenylsulfonyl)-3-azabicyclo[4.1.0]heptan-1-amine

Guidance literature:: Multi-step reaction with 5 steps

1.1: triethylamine / dichloromethane / 6 h / 20 °C

2.1: caesium carbonate / N,N-dimethyl-formamide / 0.5 h / 60 °C

2.2: 6 h / 60 °C

3.1: lithium hydroxide monohydrate; water / tetrahydrofuran; methanol / 3 h / 0 - 20 °C

4.1: bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; triethylamine / dichloromethane / 0 °C / Inert atmosphere

5.1: triisopropoxytitanium(IV) chloride / tetrahydrofuran / Inert atmosphere

5.2: 13 h / Inert atmosphere

With triisopropoxytitanium(IV) chloride; lithium hydroxide monohydrate; water; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; caesium carbonate; triethylamine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 5.1: Kulinkovich reaction / 5.2: Kulinkovich reaction;
DOI:10.1021/ol103105q

Reference yield:

: 1266347-50-5
(S)-methyl 2-(N-(but-3-en-1-yl)phenylsulfonamido)-3-(1-methyl-1H-indol-3-yl)propanoate

: 1266347-65-2
(1R,2S,6R)-N-benzyl-N-methyl-2-((1-methyl-1H-indol-3-yl)methyl)-3-(phenylsulfonyl)-3-azabicyclo[4.1.0]heptan-1-amine

Guidance literature:: Multi-step reaction with 3 steps

1.1: lithium hydroxide monohydrate; water / tetrahydrofuran; methanol / 3 h / 0 - 20 °C

2.1: bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; triethylamine / dichloromethane / 0 °C / Inert atmosphere

3.1: triisopropoxytitanium(IV) chloride / tetrahydrofuran / Inert atmosphere

3.2: 13 h / Inert atmosphere

With triisopropoxytitanium(IV) chloride; lithium hydroxide monohydrate; water; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; triethylamine; In tetrahydrofuran; methanol; dichloromethane; 3.1: Kulinkovich reaction / 3.2: Kulinkovich reaction;
DOI:10.1021/ol103105q