(R)-(-)-1-Methyl-3-pyrrolidinol Chemical Properties

Boiling point:

50-52 °C1 mm Hg(lit.)

alpha 

-7 º (c=1%, chloroform)

Density 

0.921 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.4640(lit.)

Flash point:

159 °F

storage temp. 

Inert atmosphere,Room Temperature

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

Liquid

pka

14.95±0.20(Predicted)

color 

Colorless to yellow to brown

optical activity

[α]20/D -7°, c = 1% in chloroform

Sensitive 

Air Sensitive & Hygroscopic

BRN 

4349393

InChIKey

FLVFPAIGVBQGET-RXMQYKEDSA-N

CAS DataBase Reference

104641-60-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

RIDADR 

NA 1993 / PGIII

WGK Germany 

3

HS Code 

29339900

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

(R)-(-)-1-Methyl-3-pyrrolidinol Usage And Synthesis

Chemical Properties

Brown liquid

Uses

(R)-1-Methyl-3-pyrrolidinol is a useful synthetic intermediate. It is used for asymmetric synthesis of constrained (-)-S-adenosyl-L-homocysteine (SAH) analogs as DNA methyltransferase inhibitors.

Synthesis

In a 100 mL round bottom flask, 2 g of (R)-3-hydroxypyrrolidine, 25 mL of tetrahydrofuran (THF), 0.49 g of paraformaldehyde, and 1.5 g of 90% formic acid were added sequentially. The reaction mixture was stirred under reflux conditions for 5 h (until all solids were completely dissolved), after which the reaction system was cooled to 0 °C and the pH was adjusted to about 10 by slow addition of 10 mL of 10 N sodium hydroxide solution. the organic phase was separated and dried over anhydrous magnesium sulfate. After filtration to remove the desiccant, the solvent (THF) was removed by distillation under reduced pressure to afford the oily product (R)-1-methyl-3-hydroxypyrrolidine (1.5 g, 92% yield). The product was characterized by 1H NMR (CDCl3, 300 MHz): δ 1.50-1.60 (m, 1H), 1.98-2.10 (m, 1H), 2.25 (s, 3H), 2.25-2.40 (m, 2H), 2.50-2.60 (m, 1H), 2.61-2.70 (m, 1H), 3.80 (brs, 1H), and 4.20-4.30 (m, 1H).

References

[1] Patent: US2007/123557, 2007, A1. Location in patent: Page/Page column 16
[2] Patent: WO2003/87094, 2003, A2. Location in patent: Page/Page column 34

(R)-(-)-1-Methyl-3-pyrrolidinol(104641-60-3)Related Product Information

• CHLOROPHOSPHONAZO III
• Polyvinylpyrrolidone
• Pirimiphos-methyl
• 1-Methylpyrrolidine
• 3-Pyrrolidinol
• 2,5-Dimethylpyrrolidine
• Kresoxim-methyl
• N-Methyl-2-pyrrolidone
• Pyrrolidine
• Tribenuron methyl
• Methyl acetate
• METSULFURON METHYL
• Methyl salicylate
• (S)-1-METHYL-3-PYRROLIDINOL
• Thiophanate-methyl
• Methyl
• Benzoylformic acid
• LPHE-009