(S)-3-((1R,5S,7S)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]decane-4-carbonyl)-pyrazolidine-1-carboxylic acid benzyl ester

Base Information

• Chemical Name: (S)-3-((1R,5S,7S)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]decane-4-carbonyl)-pyrazolidine-1-carboxylic acid benzyl ester
• CAS No.: 635291-65-5
• Molecular Formula: C₂₂H₂₉N₃O₅S
• Molecular Weight: 447.555

Synonyms:(S)-3-((1R,5S,7S)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]decane-4-carbonyl)-pyrazolidine-1-carboxylic acid benzyl ester

Chemical Property of (S)-3-((1R,5S,7S)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]decane-4-carbonyl)-pyrazolidine-1-carboxylic acid benzyl ester

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Technology Process of (S)-3-((1R,5S,7S)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]decane-4-carbonyl)-pyrazolidine-1-carboxylic acid benzyl ester

There total 1 articles about (S)-3-((1R,5S,7S)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]decane-4-carbonyl)-pyrazolidine-1-carboxylic acid benzyl 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: 29.0%

benzyl chloroformate (501-53-1,94274-21-2) + (3,4-dihydro-2H-pyrazol-3-yl)-(10,10-dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-methanone (193945-92-5) → (S)-3-((1R,5S,7S)-10,10-Dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]decane-4-carbonyl)-pyrazolidine-1-carboxylic acid benzyl ester (635291-65-5)

Guidance literature:

(3,4-dihydro-2H-pyrazol-3-yl)-(10,10-dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-methanone; With sodium cyanoborohydride; acetic acid; at 20 ℃; for 1h;

benzyl chloroformate; With triethylamine; In dichloromethane; at 20 ℃; for 2h;

DOI:10.1016/j.tet.2003.09.027

Reference yield: 74.0%

magnesium methanolate (109-88-6,16436-83-2,16436-85-4) + (S)-3-((1R,5S,7S)-10,10-Dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]decane-4-carbonyl)-pyrazolidine-1-carboxylic acid benzyl ester (635291-65-5) → 3-methyl 1-(phenylmethyl) (3S)-1,3-pyrazolidinedicarboxylate (635291-66-6)

Guidance literature:

In methanol; dichloromethane; at 0 - 20 ℃;

DOI:10.1016/j.tet.2003.09.027

Reference yield:

(S)-3-((1R,5S,7S)-10,10-Dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]decane-4-carbonyl)-pyrazolidine-1-carboxylic acid benzyl ester (635291-65-5) → methyl 8-oxo-6-phenylhexahydro-1H-pyrazolo[1,2-a]pyridazine-1-carboxylate

Guidance literature:

Multi-step reaction with 4 steps

1.1: 74 percent / methanol; CH₂Cl₂ / 0 - 20 °C

2.1: ozone / CH₂Cl₂

2.2: dimethyl sulfide / CH₂Cl₂

3.1: hydrogen / palladium on carbon / ethyl acetate

With hydrogen; ozone; palladium on activated charcoal; In methanol; dichloromethane; ethyl acetate;

DOI:10.1016/j.tet.2003.09.027

upstream raw materials:

benzyl chloroformate

(3,4-dihydro-2H-pyrazol-3-yl)-(10,10-dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-methanone

Downstream raw materials:

3-methyl 1-(phenylmethyl) (3S)-1,3-pyrazolidinedicarboxylate

methyl 2-[2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)pent-4-enoyl]-1-benzyloxycarbonylpyrazolidine-3-carboxylate

methyl (3S)-2-[(2S,3S)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-3-phenyl-5-oxopentanoyl]-1-benzyloxycarbonylpyrazolidine-3-carboxylate

methyl 1-benzyloxycarbonyl-2-[2-(1,3-di-oxo-1,3-dihydro-2H-isoindol-2-yl)-3-phenylpent-4-enoyl]pyrazolidine-3-carboxylate

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