N-Methyl-D-prolinol Chemical Properties

Density 

0.971 g/mL at 25 °C

refractive index 

n20/D4.469

Flash point:

71℃

storage temp. 

2-8°C

pka

14.77±0.10(Predicted)

form 

liquid

Appearance

Colorless to light yellow Liquid

optical activity

Consistent with structure

Boiling point:

68-71°C(lit.)

InChI

InChI=1S/C6H13NO/c1-7-4-2-3-6(7)5-8/h6,8H,2-5H2,1H3/t6-/m1/s1

InChIKey

VCOJPHPOVDIRJK-ZCFIWIBFSA-N

SMILES

N1(C)CCC[C@@H]1CO

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-37/38-41

Safety Statements 

26-39

RIDADR 

NA 1993 / PGIII

WGK Germany 

3

HS Code 

2933998090

N-Methyl-D-prolinol Usage And Synthesis

Uses

N-Methyl-D-prolinol is used as a pharmaceutical or synthetic intermediate component in the preparation of organic compounds such as nitrogen-containing heterocyclic compounds, pyrotinib intermediate and anidulafungin derivative.

Synthesis

Step 1: Preparation of [(2R)-1-methylpyrrolidin-2-yl]methanol Lithium aluminum hydride (230 mg, 6 mmol) and N-tert-butoxycarbonyl-R-prolinol (400 mg, 2 mmol) were dissolved in 10 mL of dry tetrahydrofuran and cooled in an ice water bath. After no significant gas release, the reaction mixture was heated to reflux and maintained for 2 hours. Upon completion of the reaction, the mixture was slowly added dropwise to 5 mL of methanol in an ice-water bath, followed by the addition of 5 mL of water. The mixture was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to afford N-methyl-D-prolinol [(2R)-1-methylpyrrolidin-2-yl]methanol (221 mg, 77.0% yield) as a colorless oil. Mass spectrum (ESI) m/z: 116 [M + 1].

References

[1] Patent: US2013/338190, 2013, A1. Location in patent: Paragraph 0037; 0038
[2] Patent: EP2684877, 2014, A2. Location in patent: Page/Page column 0032; 0033
[3] Patent: TWI524893, 2016, B. Location in patent: Page/Page column 44; 45
[4] Patent: WO2018/31877, 2018, A1. Location in patent: Paragraph 00150

N-Methyl-D-prolinol(99494-01-6)Related Product Information

• Basic Violet 1
• 3-Methyl butynol
• Methanol
• Kresoxim-methyl
• 2,2,6,6-Tetramethyl-4-piperidinol
• Methyl acetate
• Paraquat dichloride
• 4-Methyl-2-pentanol
• Methylparaben
• D(-)Prolinol
• Acetonitrile
• Methyl acrylate
• Methyl
• Methyl bromide
• (3S)-1-(tert-Butoxycarbonyl)-3-pyrrolidinecarboxylic acid
• Z-D-PYR-OH
• BOC-L-Prolinol
• (R)-alpha,alpha-Diphenylmethylprolinol