(S)-(2-((tert-butyldimethylsilyloxy)methyl)-4-(4-methoxyphenyl)-2,5-dihydro-1H-pyrrol-1-yl)(4,5-dimethoxy-2-nitrophenyl)methanone

Base Information

• Chemical Name: (S)-(2-((tert-butyldimethylsilyloxy)methyl)-4-(4-methoxyphenyl)-2,5-dihydro-1H-pyrrol-1-yl)(4,5-dimethoxy-2-nitrophenyl)methanone
• CAS No.: 637035-44-0
• Molecular Formula: C₂₇H₃₆N₂O₇Si
• Molecular Weight: 528.678

Synonyms:(S)-(2-((tert-butyldimethylsilyloxy)methyl)-4-(4-methoxyphenyl)-2,5-dihydro-1H-pyrrol-1-yl)(4,5-dimethoxy-2-nitrophenyl)methanone

Chemical Property of (S)-(2-((tert-butyldimethylsilyloxy)methyl)-4-(4-methoxyphenyl)-2,5-dihydro-1H-pyrrol-1-yl)(4,5-dimethoxy-2-nitrophenyl)methanone

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of (S)-(2-((tert-butyldimethylsilyloxy)methyl)-4-(4-methoxyphenyl)-2,5-dihydro-1H-pyrrol-1-yl)(4,5-dimethoxy-2-nitrophenyl)methanone

There total 5 articles about (S)-(2-((tert-butyldimethylsilyloxy)methyl)-4-(4-methoxyphenyl)-2,5-dihydro-1H-pyrrol-1-yl)(4,5-dimethoxy-2-nitrophenyl)methanone 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: 80.0%

4-methoxyphenylboronic acid (5720-07-0) + (S)-5-((tert-butyldimethylsilyloxy)methyl)-1-(4,5-dimethoxy-2-nitrobenzoyl)-2,5-dihydro-1H-pyrrol-3-yl trifluoromethanesulfonate (637035-43-9) → (S)-(2-((tert-butyldimethylsilyloxy)methyl)-4-(4-methoxyphenyl)-2,5-dihydro-1H-pyrrol-1-yl)(4,5-dimethoxy-2-nitrophenyl)methanone (637035-44-0)

Guidance literature:

With sodium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In ethanol; toluene; for 1h; Heating;

DOI:10.1039/b303274d

Reference yield:

4,5-dimethoxy-2-nitro-benzoic acid (4998-07-6) → (S)-(2-((tert-butyldimethylsilyloxy)methyl)-4-(4-methoxyphenyl)-2,5-dihydro-1H-pyrrol-1-yl)(4,5-dimethoxy-2-nitrophenyl)methanone (637035-44-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 70 percent / DCC; HOBt; DMF / CH₂Cl₂ / 48 h

2.1: 90 percent / iodobenzene diacetate; TEMPO / CH₂Cl₂ / 2 h

3.1: NaHMDS / tetrahydrofuran / 1 h / -78 °C

3.2: 50 percent / tetrahydrofuran / 4 h / -30 - 25 °C

4.1: 80 percent / aq. Na₂CO₃ / Pd(PPh₃)4 / toluene; ethanol / 1 h / Heating

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; [bis(acetoxy)iodo]benzene; sodium hexamethyldisilazane; sodium carbonate; benzotriazol-1-ol; N,N-dimethyl-formamide; dicyclohexyl-carbodiimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; ethanol; dichloromethane; toluene; 4.1: Suzuki reaction;

DOI:10.1039/b303274d

Reference yield:

(2S,4R)-2-tert-butyldimethylsilyloxymethyl-4-hydroxypyrrolidine (260417-94-5) → (S)-(2-((tert-butyldimethylsilyloxy)methyl)-4-(4-methoxyphenyl)-2,5-dihydro-1H-pyrrol-1-yl)(4,5-dimethoxy-2-nitrophenyl)methanone (637035-44-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 70 percent / DCC; HOBt; DMF / CH₂Cl₂ / 48 h

2.1: 90 percent / iodobenzene diacetate; TEMPO / CH₂Cl₂ / 2 h

3.1: NaHMDS / tetrahydrofuran / 1 h / -78 °C

3.2: 50 percent / tetrahydrofuran / 4 h / -30 - 25 °C

4.1: 80 percent / aq. Na₂CO₃ / Pd(PPh₃)4 / toluene; ethanol / 1 h / Heating

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; [bis(acetoxy)iodo]benzene; sodium hexamethyldisilazane; sodium carbonate; benzotriazol-1-ol; N,N-dimethyl-formamide; dicyclohexyl-carbodiimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; ethanol; dichloromethane; toluene; 4.1: Suzuki reaction;

DOI:10.1039/b303274d

upstream raw materials:

4-methoxyphenylboronic acid

(S)-5-((tert-butyldimethylsilyloxy)methyl)-1-(4,5-dimethoxy-2-nitrobenzoyl)-2,5-dihydro-1H-pyrrol-3-yl trifluoromethanesulfonate

4,5-dimethoxy-2-nitro-benzoic acid

(2S,4R)-2-tert-butyldimethylsilyloxymethyl-4-hydroxypyrrolidine

Downstream raw materials:

(S)-allyl 2-(2-((tert-butyldimethylsilyloxy)methyl)-4-(4-methoxyphenyl)-2,5-dihydro-1H-pyrrole-1-carbonyl)-4,5-dimethoxyphenylcarbamate

(S)-allyl 2-(2-(hydroxymethyl)-4-(4-methoxyphenyl)-2,5-dihydro-1H-pyrrole-1-carbonyl)-4,5-dimethoxyphenylcarbamate

(11S,11aS)-allyl 11-hydroxy-7,8-dimethoxy-2-(4-methoxyphenyl)-5-oxo-11,11a-dihydro-3H-pyrrolo[2,1-c][1,4]benzodiazepine-10(5H)-carboxylate

(S)-(2-amino-4,5-dimethoxyphenyl)(2-((tert-butyldimethylsilyloxy)methyl)-4-(4-methoxyphenyl)-2,5-dihydro-1H-pyrrol-1-yl)methanone

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