(2R,4R)-1-benzyl-2-[(4-bromo-1-methylpyrazol-5-yl)methyl]-4-tert-butyldimethylsilyloxypyrrolidine

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Chemical Name:(2R,4R)-1-benzyl-2-[(4-bromo-1-methylpyrazol-5-yl)methyl]-4-tert-butyldimethylsilyloxypyrrolidine
CAS No.:164162-02-1
Molecular Formula:C₂₂H₃₄BrN₃OSi
Molecular Weight:464.521
Hs Code.:

Synonyms:(2R,4R)-1-benzyl-2-[(4-bromo-1-methylpyrazol-5-yl)methyl]-4-tert-butyldimethylsilyloxypyrrolidine

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Chemical Property of (2R,4R)-1-benzyl-2-[(4-bromo-1-methylpyrazol-5-yl)methyl]-4-tert-butyldimethylsilyloxypyrrolidine

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Technology Process of (2R,4R)-1-benzyl-2-[(4-bromo-1-methylpyrazol-5-yl)methyl]-4-tert-butyldimethylsilyloxypyrrolidine

There total 5 articles about (2R,4R)-1-benzyl-2-[(4-bromo-1-methylpyrazol-5-yl)methyl]-4-tert-butyldimethylsilyloxypyrrolidine 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: 66.0%

: 164162-01-0
(2R,4R)-1-benzyl-4-tert-butyldimethylsilyloxy-2-[(1-methylpyrazol-5-yl)methyl]pyrrolidine

: 164162-02-1
(2R,4R)-1-benzyl-2-[(4-bromo-1-methylpyrazol-5-yl)methyl]-4-tert-butyldimethylsilyloxypyrrolidine

Guidance literature:: With bromine; sodium carbonate; In dichloromethane; at 0 ℃; for 0.5h;
DOI:10.1016/S0968-0896(00)00314-X

Reference yield:

: 156440-98-1
(2S,4R)-N-benzyl-4-(tert-butyldimethylsilyloxy)pyrrolidine-2-carbaldehyde

: 164162-02-1
(2R,4R)-1-benzyl-2-[(4-bromo-1-methylpyrazol-5-yl)methyl]-4-tert-butyldimethylsilyloxypyrrolidine

Guidance literature:: Multi-step reaction with 5 steps

1: 87.9 percent / n-BuLi / tetrahydrofuran; hexane / 3 h / -70 - 5 °C

2: SOCl₂ / 1 h / -20 °C

3: Et₃N / CH₂Cl₂ / 1 h / -15 - -5 °C

4: 47.36 g / AIBN; n-Bu₃SnH / toluene / 1.75 h / Heating

5: 66 percent / Br₂; Na₂CO₃ / CH₂Cl₂ / 0.5 h / 0 °C

With n-butyllithium; thionyl chloride; 2,2'-azobis(isobutyronitrile); bromine; tri-n-butyl-tin hydride; sodium carbonate; triethylamine; In tetrahydrofuran; hexane; dichloromethane; toluene;
DOI:10.1016/S0968-0896(00)00314-X

Reference yield:

: 351529-73-2
(RS)-[(2S,4R)-1-benzyl-4-tert-butyldimethylsilyloxypyrrolidin-2-yl]-(1-methylpyrazol-5-yl)methanol

: 164162-02-1
(2R,4R)-1-benzyl-2-[(4-bromo-1-methylpyrazol-5-yl)methyl]-4-tert-butyldimethylsilyloxypyrrolidine

Guidance literature:: Multi-step reaction with 4 steps

1: SOCl₂ / 1 h / -20 °C

2: Et₃N / CH₂Cl₂ / 1 h / -15 - -5 °C

3: 47.36 g / AIBN; n-Bu₃SnH / toluene / 1.75 h / Heating

4: 66 percent / Br₂; Na₂CO₃ / CH₂Cl₂ / 0.5 h / 0 °C

With thionyl chloride; 2,2'-azobis(isobutyronitrile); bromine; tri-n-butyl-tin hydride; sodium carbonate; triethylamine; In dichloromethane; toluene;
DOI:10.1016/S0968-0896(00)00314-X