benzyl (1S,5R)-(-)-3-trimethylsiloxy-8-azabicyclo<3.2.1>oct-2-ene-8-carboxylate

Base Information

Chemical Name:benzyl (1S,5R)-(-)-3-trimethylsiloxy-8-azabicyclo<3.2.1>oct-2-ene-8-carboxylate
CAS No.:130753-15-0
Molecular Formula:C₁₈H₂₅NO₃Si
Molecular Weight:331.487
Hs Code.:

Synonyms:benzyl (1S,5R)-(-)-3-trimethylsiloxy-8-azabicyclo<3.2.1>oct-2-ene-8-carboxylate

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of benzyl (1S,5R)-(-)-3-trimethylsiloxy-8-azabicyclo<3.2.1>oct-2-ene-8-carboxylate

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Technology Process of benzyl (1S,5R)-(-)-3-trimethylsiloxy-8-azabicyclo<3.2.1>oct-2-ene-8-carboxylate

There total 5 articles about benzyl (1S,5R)-(-)-3-trimethylsiloxy-8-azabicyclo<3.2.1>oct-2-ene-8-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: 89.0%

: 75-77-4
chloro-trimethyl-silane

: 130753-13-8
benzyl 3-oxo-8-azabicyclo[3,2,1]octane-8-carboxylate

: 130753-15-0
benzyl (1S,5R)-(-)-3-trimethylsiloxy-8-azabicyclo<3.2.1>oct-2-ene-8-carboxylate

Guidance literature:: With n-butyllithium; chiral pyrrolidine synthon; In N,N,N,N,N,N-hexamethylphosphoric triamide; at -100 ℃;
DOI:10.1248/cpb.38.2072

Reference yield: 89.0%

: 75-77-4
chloro-trimethyl-silane

: benzyl (1R,5S)-3-oxo-8-azabicyclo[3.2.1]octane-8-carboxylate

: 130753-15-0
benzyl (1S,5R)-(-)-3-trimethylsiloxy-8-azabicyclo<3.2.1>oct-2-ene-8-carboxylate

Guidance literature:: With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; (S)-tert-butyl-<2-(4-methyl-piperazin-1-yl)-1-phenyl>ethylamine; In tetrahydrofuran; hexane; 1.) -100 deg C to r.t., 1 h, 2.) -100 deg C, 2 h;

Reference yield:

: 542-05-2
acetonedicarboxylic acid

: 130753-15-0
benzyl (1S,5R)-(-)-3-trimethylsiloxy-8-azabicyclo<3.2.1>oct-2-ene-8-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1: 78 percent / aq. sodium acetate / 1.) r.t., 1 h, 2.) 50 deg C, 2 h

2: H₂ / 5percent Pd/C / acetic acid / 72 h / 60 °C

3: 10percent aq. K₂CO₃ / CH₂Cl₂ / 8 h / Ambient temperature

4: 89 percent / (S)-tert-butyl-<2-(4-methyl-piperazin-1-yl)-1-phenyl>ethylamine, BuLi, HMPA / hexane; tetrahydrofuran / 1.) -100 deg C to r.t., 1 h, 2.) -100 deg C, 2 h

With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; (S)-tert-butyl-<2-(4-methyl-piperazin-1-yl)-1-phenyl>ethylamine; hydrogen; sodium acetate; potassium carbonate; palladium on activated charcoal; In tetrahydrofuran; hexane; dichloromethane; acetic acid;