(R)-tert-butyl 3-(2-hydroxyethyl)pyrrolidine-1-carboxylate

Base Information

• Chemical Name: (R)-tert-butyl 3-(2-hydroxyethyl)pyrrolidine-1-carboxylate
• CAS No.: 1212182-03-0
• Molecular Formula: C₁₁H₂₁NO₃
• Molecular Weight: 215.293
• Mol file: 1212182-03-0.mol

Synonyms:tert-butyl (3R)-3-(2-hydroxyethyl)pyrrolidine-1-carboxylate

Chemical Property of (R)-tert-butyl 3-(2-hydroxyethyl)pyrrolidine-1-carboxylate

Chemical Property:

Purity/Quality:

97% ^*data from raw suppliers

(R)-N-Boc-3-(2-hydroxyethyl)pyrrolidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-tert-butyl 3-(2-hydroxyethyl)pyrrolidine-1-carboxylate

There total 4 articles about (R)-tert-butyl 3-(2-hydroxyethyl)pyrrolidine-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: 100.0%

(R)-3-carboxymethyl-pyrrolidin-1-carboxylic acid tert-butyl ester (204688-60-8) → tert-butyl (3R)-3-(2-hydroxyethyl)pyrrolidine-1-carboxylate (1212182-03-0)

Guidance literature:

(R)-3-carboxymethyl-pyrrolidin-1-carboxylic acid tert-butyl ester; With borane-THF; In tetrahydrofuran; at 23 - 28 ℃; for 2.75h; Inert atmosphere;

With sodium hydroxide; In tetrahydrofuran; water; at 10 - 25 ℃; for 1.66667h; Product distribution / selectivity;

Reference yield:

tert-butyl (3R)-3-methylsulfonyloxypyrrolidine-1-carboxylate (127423-61-4) → tert-butyl (3R)-3-(2-hydroxyethyl)pyrrolidine-1-carboxylate (1212182-03-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: potassium tert-butylate / 1-methyl-pyrrolidin-2-one / 35 - 40 °C

1.2: 18 h / 65 °C

1.3: pH 3 - 4

2.1: diethyl malonate; potassium hydroxide / water; tetrahydrofuran / 25 - 45 °C

2.2: 0.5 h / 5 - 10 °C

3.1: dimethyl sulfoxide / toluene / 2 h / Reflux

4.1: borane-THF / tetrahydrofuran / 2.75 h / 23 - 28 °C / Inert atmosphere

4.2: 1.67 h / 10 - 25 °C

With borane-THF; potassium tert-butylate; dimethyl sulfoxide; diethyl malonate; potassium hydroxide; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; water; toluene;

Reference yield:

2-((R)-1-tert-butoxycarbonyl-pyrrolidin-3-yl)-malonic acid diethyl ester (1228312-12-6) → tert-butyl (3R)-3-(2-hydroxyethyl)pyrrolidine-1-carboxylate (1212182-03-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: diethyl malonate; potassium hydroxide / water; tetrahydrofuran / 25 - 45 °C

1.2: 0.5 h / 5 - 10 °C

2.1: dimethyl sulfoxide / toluene / 2 h / Reflux

3.1: borane-THF / tetrahydrofuran / 2.75 h / 23 - 28 °C / Inert atmosphere

3.2: 1.67 h / 10 - 25 °C

With borane-THF; dimethyl sulfoxide; diethyl malonate; potassium hydroxide; In tetrahydrofuran; water; toluene;

upstream raw materials:

(R)-3-carboxymethyl-pyrrolidin-1-carboxylic acid tert-butyl ester

tert-butyl (3R)-3-methylsulfonyloxypyrrolidine-1-carboxylate

2-((R)-1-tert-butoxycarbonyl-pyrrolidin-3-yl)-malonic acid diethyl ester

2-((R)-1-tert-butoxycarbonyl-pyrrolidin-3-yl)-malonic acid

Downstream raw materials:

(R)-3-vinylpyrrolidine-1-carboxylic acid t-butyl ester