(1R,2R,3S,4R)-3-Amino-1,2,3,4-tetrahydro-1,4-methano-naphthalene-2-carboxylic acid ((S)-1-methylcarbamoyl-2-phenyl-ethyl)-amide

Base Information

Chemical Name:(1R,2R,3S,4R)-3-Amino-1,2,3,4-tetrahydro-1,4-methano-naphthalene-2-carboxylic acid ((S)-1-methylcarbamoyl-2-phenyl-ethyl)-amide
CAS No.:854278-97-0
Molecular Formula:C₂₂H₂₅N₃O₂
Molecular Weight:363.459
Hs Code.:

Synonyms:(1R,2R,3S,4R)-3-Amino-1,2,3,4-tetrahydro-1,4-methano-naphthalene-2-carboxylic acid ((S)-1-methylcarbamoyl-2-phenyl-ethyl)-amide

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Chemical Property of (1R,2R,3S,4R)-3-Amino-1,2,3,4-tetrahydro-1,4-methano-naphthalene-2-carboxylic acid ((S)-1-methylcarbamoyl-2-phenyl-ethyl)-amide

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Technology Process of (1R,2R,3S,4R)-3-Amino-1,2,3,4-tetrahydro-1,4-methano-naphthalene-2-carboxylic acid ((S)-1-methylcarbamoyl-2-phenyl-ethyl)-amide

There total 8 articles about (1R,2R,3S,4R)-3-Amino-1,2,3,4-tetrahydro-1,4-methano-naphthalene-2-carboxylic acid ((S)-1-methylcarbamoyl-2-phenyl-ethyl)-amide 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: 34.0%

: 854278-95-8
[(1R,2S,3R,4R)-3-((S)-1-Methylcarbamoyl-2-phenyl-ethylcarbamoyl)-1,2,3,4-tetrahydro-1,4-methano-naphthalen-2-yl]-carbamic acid methyl ester

: 854278-97-0
(1R,2R,3S,4R)-3-Amino-1,2,3,4-tetrahydro-1,4-methano-naphthalene-2-carboxylic acid ((S)-1-methylcarbamoyl-2-phenyl-ethyl)-amide

Guidance literature:: With chloro-trimethyl-silane; sodium iodide; In acetonitrile; for 20h; Heating;
DOI:10.1021/jo0479563

Reference yield:

: (1R,2R,3S,4S)-1,2,3,4-Tetrahydro-1,4-methano-naphthalene-2,3-dicarboxylic acid monomethyl ester

: 854278-97-0
(1R,2R,3S,4R)-3-Amino-1,2,3,4-tetrahydro-1,4-methano-naphthalene-2-carboxylic acid ((S)-1-methylcarbamoyl-2-phenyl-ethyl)-amide

Guidance literature:: Multi-step reaction with 6 steps

1.1: tetrahydrofuran / 0.5 h / 0 °C

2.1: 699 mg / NaN₃ / tetrahydrofuran; H₂O / 4 h / 20 °C

3.1: 74 percent / toluene / 5 h / Heating

4.1: 90 percent / LiOH*H₂O / H₂O; methanol / 3 h / 20 °C

5.1: CDI / CH₂Cl₂ / 1 h / 20 °C

5.2: 27 percent / CH₂Cl₂ / 20 °C

6.1: 34 percent / TMSCl; NaI / acetonitrile / 20 h / Heating

With lithium hydroxide; chloro-trimethyl-silane; sodium azide; 1,1'-carbonyldiimidazole; sodium iodide; In tetrahydrofuran; methanol; dichloromethane; water; toluene; acetonitrile; 3.1: Schmidt rearrangement;
DOI:10.1021/jo0479563

Reference yield:

: (1R,2R,3S,4R)-3-Methoxycarbonylamino-1,2,3,4-tetrahydro-1,4-methano-naphthalene-2-carboxylic acid

: 854278-97-0
(1R,2R,3S,4R)-3-Amino-1,2,3,4-tetrahydro-1,4-methano-naphthalene-2-carboxylic acid ((S)-1-methylcarbamoyl-2-phenyl-ethyl)-amide

Guidance literature:: Multi-step reaction with 2 steps

1.1: CDI / CH₂Cl₂ / 1 h / 20 °C

1.2: 27 percent / CH₂Cl₂ / 20 °C

2.1: 34 percent / TMSCl; NaI / acetonitrile / 20 h / Heating

With chloro-trimethyl-silane; 1,1'-carbonyldiimidazole; sodium iodide; In dichloromethane; acetonitrile;
DOI:10.1021/jo0479563