3(R)-HYDROXYMETHYLMORPHOLINE Chemical Properties

Melting point:

78-81°C

Boiling point:

218℃

Density 

1.045

Flash point:

86℃

storage temp. 

Keep in dark place,Inert atmosphere,2-8°C

solubility 

Chloroform

form 

Solid

pka

14.85±0.10(Predicted)

color 

White to Off-White

optical activity

Consistent with structure

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

3(R)-HYDROXYMETHYLMORPHOLINE Usage And Synthesis

Chemical Properties

White to Off-White Solid

Uses

A chiral morpholine drivative.

Synthesis

General procedure for the synthesis of (R)-3-hydroxymethylmorpholine from (R)-(4-benzyl-3-morpholinyl)-methanol: (a) Preparation of (3R)-morpholin-3-ylmethanol: [(3R)-4-benzylmorpholin-3-yl]methanol (cf. J. Med. Chem.; 29; 1986; 1288-1290; 1.1 g, 5.4 mmol) was dissolved in ethanol (25 mL), palladium hydroxide (20% loaded on activated carbon, 0.7 g) and acetic acid (0.5 mL). The reaction mixture was stirred overnight at room temperature under hydrogen atmosphere (1.2 bar). After completion of the reaction, the catalyst was removed by filtration and the solvent was removed by evaporation under reduced pressure. The residue except 200 mg was dissolved in ether (1 mL) and tetrahydrofuran (10 mL). The solution was purified by passing it through a strong cation exchange column (Isolute SCX-2, 10 g). The column was first washed with tetrahydrofuran, followed by elution of the target product with ammonia-saturated methanol. The solvent was removed by evaporation under reduced pressure to give 0.3625 g (57% yield) of (3R)-morpholin-3-ylmethanol as an oil.1H NMR (500 MHz, CD3OD): δ 2.9 (m, 3H), 3.3 (t, 1H), 3.5 (m, 3H), 3.7-3.9 (m, 2H).

References

[1] Patent: WO2006/137790, 2006, A1. Location in patent: Page/Page column 35
[2] Journal of Medicinal Chemistry, 2017, vol. 60, # 6, p. 2227 - 2244

3(R)-HYDROXYMETHYLMORPHOLINE(211053-49-5)Related Product Information

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• (S)-FMOC-2-CARBOXYMORPHOLINE