(1R,3S)-1-Adamantan-1-ylmethyl-9-(2-chloro-benzyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid benzyl ester

Base Information

Chemical Name:(1R,3S)-1-Adamantan-1-ylmethyl-9-(2-chloro-benzyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid benzyl ester
CAS No.:1026151-76-7
Molecular Formula:C₃₇H₃₉ClN₂O₂
Molecular Weight:579.182
Hs Code.:

Synonyms:(1R,3S)-1-Adamantan-1-ylmethyl-9-(2-chloro-benzyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid benzyl ester

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Chemical Property of (1R,3S)-1-Adamantan-1-ylmethyl-9-(2-chloro-benzyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid benzyl ester

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Technology Process of (1R,3S)-1-Adamantan-1-ylmethyl-9-(2-chloro-benzyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid benzyl ester

There total 1 articles about (1R,3S)-1-Adamantan-1-ylmethyl-9-(2-chloro-benzyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid benzyl 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:

: 18220-83-2
adamantan-1-ylacetaldehyde

: N'-(2-chlorobenzyl)-L-tryptophan benzyl ester p-toluenesulfonate

: 1026151-76-7
(1R,3S)-1-Adamantan-1-ylmethyl-9-(2-chloro-benzyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid benzyl ester

Guidance literature:: With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 23h;
DOI:10.1021/jm000960w

Reference yield:

: 1026151-76-7
(1R,3S)-1-Adamantan-1-ylmethyl-9-(2-chloro-benzyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid benzyl ester

: (3R,5S)-4-acetyl-3-[(1-adamantyl)methyl]-1-(2-chlorobenzyl)-5-(tetrazol-5-yl)methylaminocarbonyl-2,7-dioxo-2,3,4,5,6,7-hexahydro-1H-benzo[h][1,4]diazonine

Guidance literature:: Multi-step reaction with 5 steps

1.1: Et₃N; DMAP / CH₂Cl₂ / 2 h / 20 °C

2.1: O₃ / methanol / -78 °C

2.2: Me₂S / methanol / 2 h / 20 °C

3.1: H₂ / 10percent Pd/C / methanol; tetrahydrofuran / 1 h / 20 °C

4.1: PyBroPy; i-Pr₂NEt / CH₂Cl₂ / 18 h / 20 °C

5.1: 89 percent / MgBr₂*Et₂O / CH₂Cl₂ / 24 h / 20 °C

With dmap; PyBroPy; hydrogen; ozone; triethylamine; N-ethyl-N,N-diisopropylamine; magnesium bromide; 10percent Pd/C; In tetrahydrofuran; methanol; dichloromethane; 1.1: Acetylation / 2.1: ozonolysis / 2.2: Reduction / 3.1: Hydrogenolysis / 4.1: Acylation / 5.1: cleavage;
DOI:10.1021/jm000960w

Reference yield:

: 1026151-76-7
(1R,3S)-1-Adamantan-1-ylmethyl-9-(2-chloro-benzyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid benzyl ester

: 303766-95-2
(3R,5S)-4-acetyl-3-[(1-adamantyl)methyl]-1-(2-chlorobenzyl)-5-[(1S)-allyloxycarbonylethyl]aminocarbonyl-2,7-dioxo-2,3,4,5,6,7-hexahydro-1H-benzo[h][1,4]diazonine

Guidance literature:: Multi-step reaction with 4 steps

1.1: Et₃N; DMAP / CH₂Cl₂ / 2 h / 20 °C

2.1: O₃ / methanol / -78 °C

2.2: Me₂S / methanol / 2 h / 20 °C

3.1: H₂ / 10percent Pd/C / methanol; tetrahydrofuran / 1 h / 20 °C

4.1: PyBroPy; i-Pr₂NEt / CH₂Cl₂ / 18 h / 20 °C

With dmap; PyBroPy; hydrogen; ozone; triethylamine; N-ethyl-N,N-diisopropylamine; 10percent Pd/C; In tetrahydrofuran; methanol; dichloromethane; 1.1: Acetylation / 2.1: ozonolysis / 2.2: Reduction / 3.1: Hydrogenolysis / 4.1: Acylation;
DOI:10.1021/jm000960w