benzyl (1R,3S)-1-[(1-adamantyl)methyl]-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylate

Base Information

Chemical Name:benzyl (1R,3S)-1-[(1-adamantyl)methyl]-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylate
CAS No.:196947-54-3
Molecular Formula:C₃₀H₃₄N₂O₂
Molecular Weight:454.612
Hs Code.:

Synonyms:benzyl (1R,3S)-1-[(1-adamantyl)methyl]-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylate

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Chemical Property of benzyl (1R,3S)-1-[(1-adamantyl)methyl]-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylate

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Technology Process of benzyl (1R,3S)-1-[(1-adamantyl)methyl]-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylate

There total 1 articles about benzyl (1R,3S)-1-[(1-adamantyl)methyl]-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3-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: 39.0%

: 18220-83-2
adamantan-1-ylacetaldehyde

: 4299-69-8,141595-98-4
L-tryptophane benzyl ester

: 196947-54-3
benzyl (1R,3S)-1-[(1-adamantyl)methyl]-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylate

: benzyl (1S,3S)-1-[(1-adamantyl)methyl]-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylate

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

Reference yield: 93.0%

: 75-36-5
acetyl chloride

: 196947-54-3
benzyl (1R,3S)-1-[(1-adamantyl)methyl]-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylate

: 196947-56-5
benzyl (1R,3S)-1-[(1-adamantyl)methyl]-2-acetyl-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylate

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 20 ℃; for 2h;
DOI:10.1021/jm000960w

Reference yield:

: 196947-54-3
benzyl (1R,3S)-1-[(1-adamantyl)methyl]-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylate

: (13-adamantan-1-ylmethyl-11-benzyl-1,4,6,12-tetraoxo-1,2,4a,5,6,11,12,13-octahydro-4H-3,11,13a-triaza-dibenzo[a,e]cyclononen-3-yl)-acetic acid

Guidance literature:: Multi-step reaction with 9 steps

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

2.1: NaH / dimethylformamide / 0.25 h / 20 °C

2.2: dimethylformamide / 1 h

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

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

5.1: 94 percent / CF₃CO₂H / 2 h / 20 °C

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

7.1: 33 percent / Cs₂CO₃ / dimethylformamide / 2 h / 100 °C

8.1: O₃ / methanol / -78 °C

8.2: Me₂S / methanol / 2 h / 20 °C

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

With dmap; PyBroPy; hydrogen; sodium hydride; caesium carbonate; ozone; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; 10percent Pd/C; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 1.1: Acylation / 2.1: deprotonation / 2.2: Alkylation / 3.1: Hydrogenolysis / 4.1: Acylation / 5.1: acidolysis / 6.1: Acylation / 7.1: Cyclization / 8.1: ozonolysis / 8.2: Reduction / 9.1: Hydrogenolysis;
DOI:10.1021/jm000960w