tert-butyl (2S)-2-(hydroxymethyl)-2-methylpyrrolidine-1-carboxylate

Base Information

• Chemical Name: tert-butyl (2S)-2-(hydroxymethyl)-2-methylpyrrolidine-1-carboxylate
• CAS No.: 1339022-10-4
• Molecular Formula: C₁₁H₂₁NO₃
• Molecular Weight: 215.293
• Mol file: 1339022-10-4.mol

Synonyms:tert-butyl (2S)-2-(hydroxymethyl)-2-methylpyrrolidine-1-carboxylate

Chemical Property of tert-butyl (2S)-2-(hydroxymethyl)-2-methylpyrrolidine-1-carboxylate

Chemical Property:

• Boiling Point: 293.8±13.0 °C(Predicted)
• PKA: 14.77±0.10(Predicted)
• Density: 1.055±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C

Purity/Quality:

98%,99%, ^*data from raw suppliers

(2S)-1-Boc-2-methylpyrrolidine-2-methanol 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl (2S)-2-(hydroxymethyl)-2-methylpyrrolidine-1-carboxylate

There total 11 articles about tert-butyl (2S)-2-(hydroxymethyl)-2-methylpyrrolidine-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: 82.0%

→ tert-butyl (2S)-2-(hydroxymethyl)-2-methylpyrrolidine-1-carboxylate (1339022-10-4)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 20 ℃;

Reference yield:

N-(tert-butoxycarbonyl)-2-methyl-L-proline (103336-06-7) → tert-butyl (2S)-2-(hydroxymethyl)-2-methylpyrrolidine-1-carboxylate (1339022-10-4)

Guidance literature:

With borane-THF; In tetrahydrofuran; for 1h; Reflux;

DOI:10.1021/ol202381m

Reference yield:

(S)-tert-butyl 2-(2-methoxy-2-oxoethyl)-2-methylpyrrolidine-1-carboxylate → tert-butyl (2S)-2-(hydroxymethyl)-2-methylpyrrolidine-1-carboxylate (1339022-10-4)

Guidance literature:

(S)-tert-butyl 2-(2-methoxy-2-oxoethyl)-2-methylpyrrolidine-1-carboxylate; With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 ℃; for 0.5h; Inert atmosphere;

With water; In tetrahydrofuran; methanol;

upstream raw materials:

di-tert-butyl dicarbonate

N-(tert-butoxycarbonyl)-2-methyl-L-proline

(S)-1-tert-butyl 2-methyl 2-methylpyrrolidine-1,2-dicarboxylate

(S)-2-methylpyrrolidine-2-carboxylic acid

Downstream raw materials:

potassium (S)-7a-methyl-1-oxo-5,6,7,7a-tetrahydro-1H-pyrrolizine-3-carboxylate

(S)-tert-butyl 2-formyl-2-methylpyrrolidine-1-carboxylate

C₉H₁₁NO₃

(S)-benzyl (7a-methyl-1-oxo-5,6,7,7a-tetrahydro-1H-pyrrolizin-3-yl)carbamate

Refernces

• 1、 Jurica, Elizabeth A.,Wu, Ximao,Williams, Kristin N.,Hernandez, Andres S.,Nirschl, David S.,Rampulla, Richard A.,Mathur, Arvind,Zhou, Min,Cao, Gary,Xie, Chunshan,Jacob, Biji,Cai, Hong,Wang, Tao,Murphy, Brian J.,Liu, Heng,Xu, Carrie,Kunselman, Lori K.,Hicks, Michael B.,Sun, Qin,Schnur, Dora M.,Sitkoff, Doree F.,Dierks, Elizabeth A.,Apedo, Atsu,Moore, Douglas B.,Foster, Kimberly A.,Cvijic, Mary Ellen,Panemangalore, Reshma,Flynn, Neil A.,Maxwell, Brad D.,Hong, Yang,Tian, Yuan,Wilkes, Jason J.,Zinker, Bradley A.,Whaley, Jean M.,Barrish, Joel C.,Robl, Jeffrey A.,Ewing, William R.,Ellsworth, Bruce A.. "Discovery of Pyrrolidine-Containing GPR40 Agonists: Stereochemistry Effects a Change in Binding Mode". . p. 1417 - 1431. Retrieved 2017/03/08.
• 2、 Singh, Ritesh,Panda, Gautam. "L-Proline derived nitrogenous steroidal systems: An asymmetric approach to 14-azasteroids". . p. 19533 - 19544. Retrieved 2013/10/22.