(S)-2-Methylpyrrolidine hydrochloride

Base Information

• Chemical Name: (S)-2-Methylpyrrolidine hydrochloride
• CAS No.: 174500-74-4
• Molecular Formula: C₅H₁₁N*ClH
• Molecular Weight: 121.61
• Hs Code.: 2933990090
• Mol file: 174500-74-4.mol

Synonyms:Pyrrolidine,2-methyl-, hydrochloride, (2S)- (9CI);Pyrrolidine, 2-methyl-, hydrochloride,(S)-;(2S)-2-Methylpyrrolidine hydrochloride;(2S)-Methylpyrrolidinehydrochloride;(2S)-2-Methylpyrrolidine hydrochloride (1:1);(S)-2-Methylpyrrolidinehydrochloride;Pyrrolidine, 2-methyl-, (2S)-, hydrochloride (1:1);

Chemical Property of (S)-2-Methylpyrrolidine hydrochloride

Chemical Property:

• Vapor Pressure: 4.03mmHg at 25°C
• Boiling Point: 146.9 °C at 760 mmHg
• Flash Point: 42.6 °C
• PSA: 12.03000
• LogP: 1.88910
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C

Purity/Quality:

99% ^*data from raw suppliers

(S)-2-MethylpyrrolidineHydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (S)-2-Methylpyrrolidine hydrochloride

There total 6 articles about (S)-2-Methylpyrrolidine hydrochloride 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: 98.0%

2-(R)-methylpyrrolidine-1-carboxylic acid tert-butyl ester (157007-54-0) → (R)-2-methylpyrrolidine hydrochloride (41720-98-3,54677-53-1,135324-85-5,174500-74-4)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; for 0.5h;

Reference yield: 74.5%

di-tert-butyl dicarbonate (24424-99-5) + methyl (2R)-pyrrolidine-2-carboxylate (43041-12-9) + methanesulfonyl chloride (124-63-0) → (R)-2-methylpyrrolidine hydrochloride (41720-98-3,54677-53-1,135324-85-5,174500-74-4)

Guidance literature:

di-tert-butyl dicarbonate; methyl (2R)-pyrrolidine-2-carboxylate; With potassium carbonate; In methanol; at 20 ℃; for 3h; Large scale;

With sodium tetrahydroborate; In 2-methyltetrahydrofuran; at 0 ℃; for 5h; Large scale;

methanesulfonyl chloride; Further stages; Large scale;

Reference yield:

N-(tert-butoxycarbonyl)-L-prolinol (69610-40-8) → (R)-2-methylpyrrolidine hydrochloride (41720-98-3,54677-53-1,135324-85-5,174500-74-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 96 percent / Et₃N / CH₂Cl₂ / 12 h / 20 °C

2: 54 percent / LiEt₃BH / tetrahydrofuran / Heating

3: 96 percent / HCl gas / ethyl acetate / 2 h / 20 °C

With hydrogenchloride; lithium triethylborohydride; triethylamine; In tetrahydrofuran; dichloromethane; ethyl acetate;

DOI:10.1016/j.tet.2006.02.046

upstream raw materials:

2-(R)-methylpyrrolidine-1-carboxylic acid tert-butyl ester

N-(tert-butoxycarbonyl)-L-prolinol

tert-butyl (2S)-2-{[(methylsulfonyl)oxy]methyl}-pyrrolidine-1-carboxylate

(S)-2-iodomethyl-pyrrolidine-1-carboxylic acid tert-butyl ester

Downstream raw materials:

(R,2R,2'R)-2,2'-((2-iodo-1,3-phenylene)bis(oxy))bis(1-((R)-2-methylpyrrolidin-1-yl)propan-1-one)

{2-amino-6-[2-((S)-2-methylpyrrolidin-1-ylmethyl)phenyl]quinazolin-4-yl}-(1,3-dihydroisoindol-2-yl)methanone

(R)-2-methyl-1-{3-[4-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)phenoxyl]propyl}pyrrolidine

4-(2-{4-[3-((R)-2-methyl-pyrrolidin-1-yl)-propoxy]-phenyl}-2-oxo-ethyl)-piperazine-1-carboxylic acid 4-fluoro-phenyl ester

Refernces

• 1、 Mitsukura, Koichi,Suzuki, Mai,Tada, Kazuhiro,Yoshida, Toyokazu,Nagasawa, Toru. "Asymmetric synthesis of chiral cyclic amine from cyclic imine by bacterial whole-cell catalyst of enantioselective imine reductase". experimental part. p. 4533 - 4535. Retrieved 2010/11/19.
• 2、 Ku, Yi-Yin,Pu, Yu-Ming,Grieme, Tim,Sharma, Padam,Bhatia, Ashok V.,Cowart, Marlon. "An efficient and convergent synthesis of the potent and selective H3 antagonist ABT-239". . p. 4584 - 4589. Retrieved 2007/10/03.