(1S,4S,7S,8R)-6-Benzyl-11-(toluene-4-sulfonyl)-2-vinyl-6,11-diaza-tricyclo[5.4.0.0^4,8]undecane

Base Information

• Chemical Name: (1S,4S,7S,8R)-6-Benzyl-11-(toluene-4-sulfonyl)-2-vinyl-6,11-diaza-tricyclo[5.4.0.0^4,8]undecane
• CAS No.: 133627-56-2
• Molecular Formula: C₂₅H₃₀N₂O₂S
• Molecular Weight: 422.591

Synonyms:(1S,4S,7S,8R)-6-Benzyl-11-(toluene-4-sulfonyl)-2-vinyl-6,11-diaza-tricyclo[5.4.0.0^4,8]undecane

Chemical Property of (1S,4S,7S,8R)-6-Benzyl-11-(toluene-4-sulfonyl)-2-vinyl-6,11-diaza-tricyclo[5.4.0.0^4,8]undecane

Chemical Property:

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Technology Process of (1S,4S,7S,8R)-6-Benzyl-11-(toluene-4-sulfonyl)-2-vinyl-6,11-diaza-tricyclo[5.4.0.0^4,8]undecane

There total 10 articles about (1S,4S,7S,8R)-6-Benzyl-11-(toluene-4-sulfonyl)-2-vinyl-6,11-diaza-tricyclo[5.4.0.0^4,8]undecane 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: 61.0%

(3R,3aS,7aR)-1-Benzyl-6-(toluene-4-sulfonyl)-3-((E)-4-trimethylsilanyl-but-2-enyl)-octahydro-pyrrolo[2,3-c]pyridin-7-ol (133627-55-1) → (1S,4S,7S,8R)-6-Benzyl-11-(toluene-4-sulfonyl)-2-vinyl-6,11-diaza-tricyclo[5.4.0.04,8]undecane (133627-56-2)

Guidance literature:

With iron(III) chloride; In dichloromethane; -78 deg C to rt;

DOI:10.1021/jo00010a006

Reference yield:

methyl 1-benzylaziridine-2-carboxylate (21384-53-2,31907-91-2,196965-62-5) → (1S,4S,7S,8R)-6-Benzyl-11-(toluene-4-sulfonyl)-2-vinyl-6,11-diaza-tricyclo[5.4.0.04,8]undecane (133627-56-2)

Guidance literature:

Multi-step reaction with 10 steps

1: KOTMS / tetrahydrofuran

2: CH₂Cl₂

3: DMAP

4: 73 percent / 1,2-dichloro-benzene / 320 °C

5: 1) BBr₃ / 1) CH₂Cl₂, 0 deg C, 2) Swern oxidation

6: 2) Et₃N, DMAP / 1) THF, 0 deg C to rt, 2) CH₂Cl₂

7: 50 percent / HMPA / tetrahydrofuran / -25 °C

8: 1) Na/NH₃, 2) LiHMDS, DMAP / 1) t-BuOH, THF, -78 deg C, 2) THF

9: 93 percent / DIBALH / CH₂Cl₂ / -78 deg C to rt

10: 61 percent / FeCl₃ / CH₂Cl₂ / -78 deg C to rt

With N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; potassium trimethylsilonate; ammonia; sodium; boron tribromide; iron(III) chloride; diisobutylaluminium hydride; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; 1,2-dichloro-benzene;

DOI:10.1021/jo00010a006

Reference yield:

C15H19NO3 → (1S,4S,7S,8R)-6-Benzyl-11-(toluene-4-sulfonyl)-2-vinyl-6,11-diaza-tricyclo[5.4.0.04,8]undecane (133627-56-2)

Guidance literature:

Multi-step reaction with 8 steps

1: DMAP

2: 73 percent / 1,2-dichloro-benzene / 320 °C

3: 1) BBr₃ / 1) CH₂Cl₂, 0 deg C, 2) Swern oxidation

4: 2) Et₃N, DMAP / 1) THF, 0 deg C to rt, 2) CH₂Cl₂

5: 50 percent / HMPA / tetrahydrofuran / -25 °C

6: 1) Na/NH₃, 2) LiHMDS, DMAP / 1) t-BuOH, THF, -78 deg C, 2) THF

7: 93 percent / DIBALH / CH₂Cl₂ / -78 deg C to rt

8: 61 percent / FeCl₃ / CH₂Cl₂ / -78 deg C to rt

With N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; ammonia; sodium; boron tribromide; iron(III) chloride; diisobutylaluminium hydride; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; 1,2-dichloro-benzene;

DOI:10.1021/jo00010a006

upstream raw materials:

(3R,3aS,7aR)-1-Benzyl-6-(toluene-4-sulfonyl)-3-((E)-4-trimethylsilanyl-but-2-enyl)-octahydro-pyrrolo[2,3-c]pyridin-7-ol

methyl 1-benzylaziridine-2-carboxylate

((3R,3aS,7aR)-1,6-Dibenzyl-7-oxo-octahydro-pyrrolo[2,3-c]pyridin-3-yl)-acetaldehyde

(3R,3aS,7aR)-1,6-Dibenzyl-3-((E)-4-trimethylsilanyl-but-2-enyl)-octahydro-pyrrolo[2,3-c]pyridin-7-one

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