N-Methyl-L-prolinol

Base Information

• Chemical Name: N-Methyl-L-prolinol
• CAS No.: 34381-71-0
• Molecular Formula: C6H13NO
• Molecular Weight: 115.175
• Hs Code.: 29339900
• European Community (EC) Number: 251-981-9
• DSSTox Substance ID: DTXSID901295001
• Nikkaji Number: J250.870B
• Mol file: 34381-71-0.mol

Synonyms:N-Methyl-L-prolinol;34381-71-0;(S)-(-)-1-Methyl-2-pyrrolidinemethanol;[(2S)-1-methylpyrrolidin-2-yl]methanol;(S)-(1-methylpyrrolidin-2-yl)methanol;2-Pyrrolidinemethanol, 1-methyl-, (2S)-;N-methylprolinol;(S)-(-)-2-Hydroxymethyl-1-methylpyrrolidine;(S)-N-methylpyrrolidine-2-methanol;MFCD00011727;(2S)-1-Methyl-2-pyrrolidinemethanol;(S)-2-Hydroxymethyl-1-methylpyrrolidine;[(2S)-1-methyl-2-pyrrolidinyl]methanol;1-Methyl-L-prolinol;(S)-Methylpyrrolidine-2-methanol;EINECS 251-981-9;(1-Methyl-2-pyrrolidinyl)methanol #;N-methyl prolinol;SCHEMBL84792;(S)-(-)-1-Methyl-prolinol;DTXSID901295001;1-methyl-2(S)-pyrrolidinemethanol;1-Methylpyrrolidine-2alpha-methanol;(S)-1-methyl-2-pyrrolidinemethanol;(S)-1-methylpyrrolidin-2-ylmethanol;BBL103806;STL557616;AKOS016842484;(2S)-1-Methylpyrrolidin-2-ylmethanol;SMP2_000094;(S)-1-methyl-2-hydroxymethylpyrrolidine;(2S)-2-hydroxymethyl-1-methylpyrrolidine;AC-24075;DS-14511;((S)-1-Methyl-pyrrolidin-2-yl)-methanol;(S)-(1-methyl-pyrrolidin-2-yl)-methanol;2-Pyrrolidinemethanol, 1-methyl-, (S)-;(2S)-(-)-1-methyl-2-pyrrolidinemethanol;(S)-(-)-1-Methyl-2-pyrrolidine methanol;(2S)-2-(hydroxymethyl)-1-methylpyrrolidine;CS-0030792;M2058;(S)-(-)-1-methyl-2-hydroxymethylpyrrolidine;EN300-95661;(S)-(+)-2-(Hydroxymethyl)-1-methylpyrrolidine;(S)-(-)-1-Methyl-2-pyrrolidinemethanol, 96%;A822206;Q-101778

Chemical Property of N-Methyl-L-prolinol

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 0.649mmHg at 25°C
• Refractive Index: n20/D 1.469(lit.)
• Boiling Point: 164.8 °C at 760 mmHg
• PKA: 14.77±0.10(Predicted)
• Flash Point: 63.3 °C
• PSA: 23.47000
• Density: 0.973 g/cm³
• LogP: 0.01080
• Storage Temp.: −20°C
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 115.099714038
• Heavy Atom Count: 8
• Complexity: 74.9

Purity/Quality:

99% ^*data from raw suppliers

(S)?-?(-?)?-?1-?Methyl-?2-?pyrrolidinemethanol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 23-24/25-36-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1CCCC1CO
• Isomeric SMILES: CN1CCC[C@H]1CO
• Uses: N-Methyl-L-prolinol is a reagent used in the synthesis of novel 4-hydroxytamoxifen analogs used as estrogen-related receptor γ (ERRγ) inverse agonists. Precursor to phosphine ligands for catalytic asymmetric Grignard cross-coupling reactions.

Technology Process of N-Methyl-L-prolinol

There total 31 articles about N-Methyl-L-prolinol 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: 90.0%

(S)-N-(tert-butoxycarbonyl)proline methyl ester (59936-29-7) → (S)-2-hydroxymethyl-1-methylpyrrolidine (34381-71-0)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether;

DOI:10.1016/S0040-4039(00)86026-8

Reference yield: 77.0%

N-(tert-butoxycarbonyl)-L-prolinol (69610-40-8) → (S)-2-hydroxymethyl-1-methylpyrrolidine (34381-71-0)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 ℃; for 2.66667h; Reflux;

Reference yield: 65.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + (S)-1-Pyrrolidin-2-yl-methanol (23356-96-9) → (S)-2-hydroxymethyl-1-methylpyrrolidine (34381-71-0)

Guidance literature:

With formic acid; In water; for 20h; Heating;

DOI:10.1021/jo062059f

upstream raw materials:

formaldehyd

(S)-1-Pyrrolidin-2-yl-methanol

(S)-N-(tert-butoxycarbonyl)proline methyl ester

(2S)-1-formylpyrrolidine-2-carboxylic acid

Downstream raw materials:

(S)-2-(chloromethyl)-1-methylpyrrolidine

(S)-N-methylpyrrolidine-2-carboxaldehyde

4-methyl 1-{[(2S)-1-methylpyrrolidin-2-yl]methyl} 4-{[(4-phenyl-3,6-dihydropyridin-1(2H)-yl)sulfonyl]methyl}piperidine-1,4-dicarboxylate

(R)-1-methyl-2-((5-nitro-2-(trifluoromethyl)phenoxy)methyl)-pyrrolidine

Refernces

• 1、 Coleman-Kammula, S.,Duim-Koolstra, E. Th.. "ENANTIOSELECTIVE EPOXIDATION OF AN ALLYLIC ALCOHOL CATALYZED BY (ACETYLACETONATO)(L-N-METHYLPROLINOL)DIOXOMOLYBDENUM. THE DECREASE OF ENANTIOSELECTIVITY WITH CHEMICAL CONVERSION". . p. 53 - 56. Retrieved 1983.
• 2、 -. "FUMAGILLOL COMPOUNDS AND METHODS OF MAKING AND USING SAME". . . Retrieved 2018/03/06.
• 3、 -. "6-AMINO QUINAZOLINE OR 3-CYANO QUINOLINE DERIVATIVES, PREPARATION PROCESS AND PHARMACEUTICAL USE THEREOF". Page/Page column 44; 45. . Retrieved 2016/10/08.