(S)-(+)-2-(N-MethylaMino)-3-phenylpropanol Chemical Properties

Melting point:

68-70℃

Boiling point:

294.9±20.0 °C(Predicted)

Density 

1.020±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

pka

14.75±0.10(Predicted)

Appearance

White to off-white Solid

optical activity

Consistent with structure

Safety Information

RIDADR 

UN3259

HazardClass 

8

HS Code 

2922190090

(S)-(+)-2-(N-MethylaMino)-3-phenylpropanol Usage And Synthesis

Uses

N-Methyl-(S)-phenylalaninol is used in the synthesis of cyclopropane-fused oxazepanones which have antimycobacterial properties.

Synthesis

General procedure for the synthesis of (S)-(+)-2-(N-methylamino)-3-phenyl-1-propanol from 2-Boc-methylamino-3-phenyl-1-propanol: M: Deprotection of acid-unstable protecting groups (version 1) Dissolve 5 mmol of the feedstock in a wet trifluoroacetic acid-dichloromethane mixture (1:1, v/v) and stir the reaction for 4-7 hours. After completion of the reaction, the solvent was removed from the reaction mixture by evaporation. The residue was dissolved in dichloromethane and evaporated again to completely remove the residual trifluoroacetic acid. This dissolution-evaporation process was repeated three times to ensure complete removal of the acid. Finally, the residue was purified by column chromatography (using a dichloromethane-pentane gradient elution with an amino stationary phase) to give the target product. b) Synthesis of (S)-2-methylamino-3-phenyl-propan-1-ol (Ib) Compound Ia was subjected to deprotection reaction according to General Method M. Compound Ib was successfully obtained in 77% yield (630 mg, 3.8 mmol). Mass spectrometry (MS-ESI) analysis showed m/z 166 ([M + H]+, 100%). The results of the elemental analysis were consistent with the theoretical values: calculated values (%): C 72.69, H 9.15, N 8.48; measured values (%): C 72.66, H 9.13, N 8.47.

References

[1] Patent: WO2009/52970, 2009, A2. Location in patent: Page/Page column 68; 71