Thioacetic acid S-((1S,8S,9S)-10,10-dimethyl-5-phenyl-6-aza-tricyclo[7.1.1.0^2,7]undeca-2⁽⁷⁾,3,5-trien-8-ylmethyl) ester

Base Information

• Chemical Name: Thioacetic acid S-((1S,8S,9S)-10,10-dimethyl-5-phenyl-6-aza-tricyclo[7.1.1.0^2,7]undeca-2⁽⁷⁾,3,5-trien-8-ylmethyl) ester
• CAS No.: 211874-92-9
• Molecular Formula: C₂₁H₂₃NOS
• Molecular Weight: 337.486

Synonyms:Thioacetic acid S-((1S,8S,9S)-10,10-dimethyl-5-phenyl-6-aza-tricyclo[7.1.1.0^2,7]undeca-2⁽⁷⁾,3,5-trien-8-ylmethyl) ester

Chemical Property of Thioacetic acid S-((1S,8S,9S)-10,10-dimethyl-5-phenyl-6-aza-tricyclo[7.1.1.0^2,7]undeca-2⁽⁷⁾,3,5-trien-8-ylmethyl) ester

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Technology Process of Thioacetic acid S-((1S,8S,9S)-10,10-dimethyl-5-phenyl-6-aza-tricyclo[7.1.1.0^2,7]undeca-2⁽⁷⁾,3,5-trien-8-ylmethyl) ester

There total 4 articles about Thioacetic acid S-((1S,8S,9S)-10,10-dimethyl-5-phenyl-6-aza-tricyclo[7.1.1.0^2,7]undeca-2⁽⁷⁾,3,5-trien-8-ylmethyl) 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: 52.0%

Methanesulfonic acid (1S,8S,9S)-10,10-dimethyl-5-phenyl-6-aza-tricyclo[7.1.1.02,7]undeca-2(7),3,5-trien-8-ylmethyl ester (211874-91-8) + potassium thioacetate (10387-40-3) → Thioacetic acid S-((1S,8S,9S)-10,10-dimethyl-5-phenyl-6-aza-tricyclo[7.1.1.02,7]undeca-2(7),3,5-trien-8-ylmethyl) ester (211874-92-9)

Guidance literature:

In ethanol; for 15h; Heating;

DOI:10.1016/S0957-4166(98)00167-0

Reference yield:

(1S,9S)-10,10-dimethyl-5-phenyl-6-azatricyclo[7.1.1.0 2,7]undeca-2,4,6-triene (211874-85-0) → Thioacetic acid S-((1S,8S,9S)-10,10-dimethyl-5-phenyl-6-aza-tricyclo[7.1.1.02,7]undeca-2(7),3,5-trien-8-ylmethyl) ester (211874-92-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) BuLi, TMEDA / 1.) THF, a) -78 deg C, 1 h, b) -30 deg C, 2 h, 2.) THF, from -60 deg C to RT

2: 21 percent / NaBH₄, aq. Na₂CO₃ / methanol / 5 h

3: 0.65 g / Et₃N, DMAP / CH₂Cl₂ / 2 h / Ambient temperature

4: 52 percent / ethanol / 15 h / Heating

With dmap; sodium tetrahydroborate; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; sodium carbonate; triethylamine; In methanol; ethanol; dichloromethane;

DOI:10.1016/S0957-4166(98)00167-0

Reference yield:

[(1S,9R)-10,10-Dimethyl-5-phenyl-6-aza-tricyclo[7.1.1.02,7]undeca-2(7),3,5-trien-(8E)-ylidene]-methanol (211874-88-3) → Thioacetic acid S-((1S,8S,9S)-10,10-dimethyl-5-phenyl-6-aza-tricyclo[7.1.1.02,7]undeca-2(7),3,5-trien-8-ylmethyl) ester (211874-92-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 21 percent / NaBH₄, aq. Na₂CO₃ / methanol / 5 h

2: 0.65 g / Et₃N, DMAP / CH₂Cl₂ / 2 h / Ambient temperature

3: 52 percent / ethanol / 15 h / Heating

With dmap; sodium tetrahydroborate; sodium carbonate; triethylamine; In methanol; ethanol; dichloromethane;

DOI:10.1016/S0957-4166(98)00167-0

upstream raw materials:

Methanesulfonic acid (1S,8S,9S)-10,10-dimethyl-5-phenyl-6-aza-tricyclo[7.1.1.0^2,7]undeca-2⁽⁷⁾,3,5-trien-8-ylmethyl ester

potassium thioacetate

(1S,9S)-10,10-dimethyl-5-phenyl-6-azatricyclo[7.1.1.0 ^2,7]undeca-2,4,6-triene

[(1S,9R)-10,10-Dimethyl-5-phenyl-6-aza-tricyclo[7.1.1.0^2,7]undeca-2⁽⁷⁾,3,5-trien-(8E)-ylidene]-methanol

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