(2R,3R)-3-(3-Cyclopentyloxy-4-methoxy-phenyl)-1-((1R,5S,7S)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-3-phenyl-2-pyridin-4-yl-propan-1-one

Base Information

• Chemical Name: (2R,3R)-3-(3-Cyclopentyloxy-4-methoxy-phenyl)-1-((1R,5S,7S)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-3-phenyl-2-pyridin-4-yl-propan-1-one
• CAS No.: 468737-13-5
• Molecular Formula: C₃₆H₄₂N₂O₅S
• Molecular Weight: 614.806

Synonyms:

Chemical Property of (2R,3R)-3-(3-Cyclopentyloxy-4-methoxy-phenyl)-1-((1R,5S,7S)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-3-phenyl-2-pyridin-4-yl-propan-1-one

Chemical Property:

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Technology Process of (2R,3R)-3-(3-Cyclopentyloxy-4-methoxy-phenyl)-1-((1R,5S,7S)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-3-phenyl-2-pyridin-4-yl-propan-1-one

There total 7 articles about (2R,3R)-3-(3-Cyclopentyloxy-4-methoxy-phenyl)-1-((1R,5S,7S)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-3-phenyl-2-pyridin-4-yl-propan-1-one 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: 76.0%

phenylmagnesium bromide + (E)-3-(3-Cyclopentyloxy-4-methoxy-phenyl)-1-((1R,5S,7S)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-2-pyridin-4-yl-propenone (170985-18-9) → (2R,3R)-3-(3-Cyclopentyloxy-4-methoxy-phenyl)-1-((1R,5S,7S)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-3-phenyl-2-pyridin-4-yl-propan-1-one (468737-13-5)

Guidance literature:

In tetrahydrofuran;

DOI:10.1016/S0960-894X(02)00202-0

Reference yield:

isovanillin (621-59-0) → (2R,3R)-3-(3-Cyclopentyloxy-4-methoxy-phenyl)-1-((1R,5S,7S)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-3-phenyl-2-pyridin-4-yl-propan-1-one (468737-13-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 95 percent / Cs₂CO₃ / dimethylformamide

2: 58 percent / TsOH; piperidine / toluene

3: NaOH

4: SOCl₂

5: tetrahydrofuran

6: 76 percent / tetrahydrofuran

With piperidine; sodium hydroxide; thionyl chloride; caesium carbonate; toluene-4-sulfonic acid; In tetrahydrofuran; N,N-dimethyl-formamide; toluene; 2: Knoevenagel condensation / 6: Michael reaction;

DOI:10.1016/S0960-894X(02)00202-0

Reference yield:

Cyclopentyl bromide (137-43-9) → (2R,3R)-3-(3-Cyclopentyloxy-4-methoxy-phenyl)-1-((1R,5S,7S)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-3-phenyl-2-pyridin-4-yl-propan-1-one (468737-13-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 95 percent / Cs₂CO₃ / dimethylformamide

2: 58 percent / TsOH; piperidine / toluene

3: NaOH

4: SOCl₂

5: tetrahydrofuran

6: 76 percent / tetrahydrofuran

With piperidine; sodium hydroxide; thionyl chloride; caesium carbonate; toluene-4-sulfonic acid; In tetrahydrofuran; N,N-dimethyl-formamide; toluene; 2: Knoevenagel condensation / 6: Michael reaction;

DOI:10.1016/S0960-894X(02)00202-0

upstream raw materials:

(E)-3-(3-Cyclopentyloxy-4-methoxy-phenyl)-1-((1R,5S,7S)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-2-pyridin-4-yl-propenone

isovanillin

Cyclopentyl bromide

3-cyclopentyloxy-4-methoxybenzylaldehyde

Downstream raw materials:

R-(+)-4-(2-(3-cyclopentyloxy-4-methoxyphenyl)-2-phenylethyl)pyridine

(2R,3R)-3-(3-Cyclopentyloxy-4-methoxy-phenyl)-3-phenyl-2-pyridin-4-yl-thiopropionic acid S-propyl ester

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