(3R,4R)-tert-butyl 3-(hydroxymethyl)-4-methoxypyrrolidine-1-carboxylate

Base Information

• Chemical Name: (3R,4R)-tert-butyl 3-(hydroxymethyl)-4-methoxypyrrolidine-1-carboxylate
• CAS No.: 1428775-91-0
• Molecular Formula: C₁₁H₂₁NO₄
• Molecular Weight: 231.292
• Mol file: 1428775-91-0.mol

Synonyms:

Chemical Property of (3R,4R)-tert-butyl 3-(hydroxymethyl)-4-methoxypyrrolidine-1-carboxylate

Chemical Property:

Purity/Quality:

97% ^*data from raw suppliers

rel-tert-butyl(3R,4R)-3-(hydroxymethyl)-4-methoxypyrrolidine-1-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4R)-tert-butyl 3-(hydroxymethyl)-4-methoxypyrrolidine-1-carboxylate

There total 2 articles about (3R,4R)-tert-butyl 3-(hydroxymethyl)-4-methoxypyrrolidine-1-carboxylate 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:

(3S,4R)-1-benzyl-4-methoxy-pyrrolidine-3-carboxylic acid methyl ester (1428775-88-5) → tert-butyl (3R,4R)-3-(hydroxymethyl)-4-methoxypyrrolidine-1-carboxylate (1428775-91-0)

Guidance literature:

Multi-step reaction with 2 steps

1: palladium(II) hydroxide; hydrogen / ethanol / 775.74 Torr

2: lithium borohydride / tetrahydrofuran / 4 h / 60 °C

With lithium borohydride; hydrogen; palladium(II) hydroxide; In tetrahydrofuran; ethanol;

Reference yield:

methyl (3SR,4RS)-1-benzyl-4-methoxypyrrolidine-3-carboxylate → tert-butyl (3R,4R)-3-(hydroxymethyl)-4-methoxypyrrolidine-1-carboxylate (1428775-91-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: Chiralpak AD-H / methanol; diethylamine / Resolution of racemate

2.1: hydrogen; palladium(II) hydroxide / ethanol / 775.74 Torr

2.2: 1 h

3.1: lithium borohydride / tetrahydrofuran / 4 h / 60 °C

With lithium borohydride; hydrogen; palladium(II) hydroxide; In tetrahydrofuran; methanol; ethanol; diethylamine;

DOI:10.1021/acs.jmedchem.5b01633

Reference yield:

tert-butyl (3R,4R)-3-(hydroxymethyl)-4-methoxypyrrolidine-1-carboxylate (1428775-91-0) → 1-{(3R,4R)-3-[({5-chloro-2-[(1-methyl-1H-pyrazol-4-yl)amino]-7H-pyrrolo[2,3-d]pyrimidin-4-yl}oxy)methyl]-4-methoxypyrrolidin-1-yl}prop-2-en-1-one (1428774-45-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: potassium 2-methylbutan-2-olate / 1,4-dioxane; toluene / 0.5 h / 20 °C

2.1: [2-(di-tert-butylphosphino)-2′,4′,6′-triisopropyl-1,1′-biphenyl][2-((2-aminoethyl)phenyl)]palladium(II) chloride / toluene / 1 h / 90 °C

3.1: trifluoroacetic acid / dichloromethane / 2.5 h / 20 °C

4.1: sodium hydrogencarbonate / water; ethyl acetate / 0.17 h / 0 °C

4.2: 0.5 h / 20 °C

With [2-(di-tert-butylphosphino)-2′,4′,6′-triisopropyl-1,1′-biphenyl][2-((2-aminoethyl)phenyl)]palladium(II) chloride; potassium 2-methylbutan-2-olate; sodium hydrogencarbonate; trifluoroacetic acid; In 1,4-dioxane; dichloromethane; water; ethyl acetate; toluene; 2.1: |Buchwald-Hartwig Coupling;

DOI:10.1021/acs.jmedchem.5b01633

upstream raw materials:

(3S,4R)-1-benzyl-4-methoxy-pyrrolidine-3-carboxylic acid methyl ester

Downstream raw materials:

1-{(3R,4R)-3-[({5-chloro-2-[(1-methyl-1H-pyrazol-4-yl)amino]-7H-pyrrolo[2,3-d]pyrimidin-4-yl}oxy)methyl]-4-methoxypyrrolidin-1-yl}prop-2-en-1-one

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