(R)-3-Methylpyrrolidine

Base Information

• Chemical Name: (R)-3-Methylpyrrolidine
• CAS No.: 69498-24-4
• Molecular Formula: C5H11N
• Molecular Weight: 85.15
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID40452408
• Nikkaji Number: J785.183I
• Wikidata: Q72497112
• Mol file: 69498-24-4.mol

Synonyms:(R)-3-METHYLPYRROLIDINE;(3R)-3-methylpyrrolidine;69498-24-4;Pyrrolidine, 3-methyl-, (3R)-;3-r-methylpyrrolidine;3alpha-Methylpyrrolidine;(R,S)-3-Methyl-pyrrolidine;DTXSID40452408;KYINPWAJIVTFBW-RXMQYKEDSA-N;AKOS006281865;CS-0183090;EN300-725097

Chemical Property of (R)-3-Methylpyrrolidine

Chemical Property:

• Vapor Pressure: 37.103mmHg at 25°C
• Refractive Index: 1.42
• Boiling Point: 100.165 °C at 760 mmHg
• PKA: 10.53±0.10(Predicted)
• Flash Point: 0.527 °C
• PSA: 12.03000
• Density: 0.813 g/cm³
• LogP: 0.94460
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 85.089149355
• Heavy Atom Count: 6
• Complexity: 43.2

Purity/Quality:

98%Min ^*data from raw suppliers

(R)-3-Methylpyrrolidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCNC1
• Isomeric SMILES: C[C@@H]1CCNC1
• Uses: (R)-3-Methylpyrrolidine is used as a reactant in preparation of aryl indoles as highly selective ligands for estrogen receptor α (ERα). (R)-3-Methylpyrrolidine is also used in the preparation of benzazepineylidene acetamide derivatives as arginine vasopressin V2 receptor agonists.

Technology Process of (R)-3-Methylpyrrolidine

There total 3 articles about (R)-3-Methylpyrrolidine 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:

1-((2S,4aS,7R,8aR)-4,4,7-Trimethyl-2-phenylselanylmethyl-hexahydro-benzo[e][1,3]oxazin-3-yl)-propenone (235094-13-0) → (R)-3-methylpyrrolidine (69498-24-4)

Guidance literature:

Multi-step reaction with 3 steps

1: tri-n-butyltin hydride, AIBN / benzene / Heating

2: aluminium hydride / tetrahydrofuran / -10 °C

3: 1.) PCC, 4 A mol. sieves, 2.) KOH / 2.) water, THF, MeOH

With aluminium hydride; potassium hydroxide; 2,2'-azobis(isobutyronitrile); 4 A molecular sieve; tri-n-butyl-tin hydride; pyridinium chlorochromate; In tetrahydrofuran; benzene;

DOI:10.1016/S0040-4039(96)02091-6

Reference yield:

(2R,3aS,4aR,6R,8aS)-2,6,9,9-Tetramethyl-octahydro-benzo[e]pyrrolo[2,1-b][1,3]oxazin-1-one (186597-26-2) → (R)-3-methylpyrrolidine (69498-24-4)

Guidance literature:

Multi-step reaction with 2 steps

1: aluminium hydride / tetrahydrofuran / -10 °C

2: 1.) PCC, 4 A mol. sieves, 2.) KOH / 2.) water, THF, MeOH

With aluminium hydride; potassium hydroxide; 4 A molecular sieve; pyridinium chlorochromate; In tetrahydrofuran;

DOI:10.1016/S0040-4039(96)02091-6

Reference yield:

(3'R)-8-(3'-methylpyrrolidinyl)menthol (186597-30-8) → (R)-3-methylpyrrolidine (69498-24-4)

Guidance literature:

With potassium hydroxide; 4 A molecular sieve; pyridinium chlorochromate; Multistep reaction; 2.) water, THF, MeOH;

DOI:10.1016/S0040-4039(96)02091-6

upstream raw materials:

(3'R)-8-(3'-methylpyrrolidinyl)menthol

1-((2S,4aS,7R,8aR)-4,4,7-Trimethyl-2-phenylselanylmethyl-hexahydro-benzo[e][1,3]oxazin-3-yl)-propenone

(2R,3aS,4aR,6R,8aS)-2,6,9,9-Tetramethyl-octahydro-benzo[e]pyrrolo[2,1-b][1,3]oxazin-1-one

Downstream raw materials:

(R)-methyl 4-(3-methylpyrrolidin-1-yl)-2-(trifluoromethyl)benzoate

(R)-methyl 2-chloro-4-(3-methylpyrrolidin-1-yl)benzoate

N-[1-(3-methyl-1-{4-[2-(3-methyl-pyrrolidin-1-yl)-ethoxy]-benzyl}-5-triisopropylsilanyloxy-1H-indol-2-yl)-ethyl]-2-(2-phenyl-1H-indol-3-yl)-acetamide

1-(3-methyl-1-{4-[2-(3-methyl-pyrrolidin-1-yl)-ethoxy]-benzyl}-5-triisopropylsilanyloxy-1H-indol-2-yl)-ethylamine

Refernces