N-BENZYL-L-ALANINOL Chemical Properties

Melting point:

47-49 °C(Solv: cyclohexane (110-82-7); ligroine (8032-32-4))

Boiling point:

120-122 °C(Press: 6 Torr)

Density 

1.020±0.06 g/cm3(Predicted)

storage temp. 

2-8°C(protect from light)

solubility 

Chloroform; Methanol;

form 

Solid

pka

14.59±0.10(Predicted)

color 

White

Safety Information

HS Code 

2922190090

N-BENZYL-L-ALANINOL Usage And Synthesis

Uses

(S)-2-(Benzylamino)propan-1-ol is a useful research chemical for the preparation of cross-benzoin products of heteroaromatic aldehydes and amino aldehydes.

Synthesis

Step 1: (S)-2-Amino-1-propanol (17.5 g, 233 mmol), benzaldehyde (26 g) and anhydrous magnesium sulfate (70 g) were dissolved in dichloromethane and the reaction was stirred for 19 hours at 25 °C. After completion of the reaction, the reaction solution was filtered and concentrated to give a yellow solid. The residue was dissolved in methanol and cooled to 0 °C. Sodium borohydride (11 g, 288 mmol) was added in batches at 0 °C (note gas generation). After addition, the reaction solution was continued to stir at 25°C for 18 hours. The reaction solution was concentrated and the residue was carefully quenched with 3M aqueous hydrochloric acid (note gas emission and exothermic phenomena). The aqueous phase was extracted with ether (4 x 200 mL). The aqueous phase was cooled to 0 °C and the pH was adjusted to 11-12 by the addition of sodium hydroxide pellets.The aqueous phase was extracted with dichloromethane, the organic phases were combined and dried with anhydrous magnesium sulfate. The dried organic phase was filtered and concentrated to give 23.2 g (60% yield) of the target product (S)-2-(benzylamino)propan-1-ol as a white solid.

References

[1] Tetrahedron, 1996, vol. 52, # 48, p. 15157 - 15170
[2] Synthetic Communications, 1994, vol. 24, # 10, p. 1415 - 1424
[3] Patent: WO2009/5646, 2009, A2. Location in patent: Page/Page column 219-220
[4] Tetrahedron Letters, 1995, vol. 36, # 46, p. 8391 - 8394
[5] Patent: US2006/14948, 2006, A1. Location in patent: Page/Page column 11

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