N-BOC-(R)-1-AMINO-2-PROPANOL Chemical Properties

Boiling point:

276.4±23.0 °C(Predicted)

Density 

1.025±0.06 g/cm3(Predicted)

refractive index 

1.4460

storage temp. 

2-8°C

pka

12.42±0.46(Predicted)

Appearance

Colorless to light yellow Viscous Liquid

InChI

InChI=1S/C8H17NO3/c1-6(10)5-9-7(11)12-8(2,3)4/h6,10H,5H2,1-4H3,(H,9,11)/t6-/m1/s1

InChIKey

YNJCFDAODGKHAV-ZCFIWIBFSA-N

SMILES

C(OC(C)(C)C)(=O)NC[C@H](O)C

CAS DataBase Reference

119768-44-4

Safety Information

HS Code 

2924297099

N-BOC-(R)-1-AMINO-2-PROPANOL Usage And Synthesis

Chemical Properties

Clear colorless liquid

Synthesis

Step 1: 1-Amino-2-propanol (compound 42.1; 3.53 g, 47.0 mmol) and triethylamine (25 mL) were dissolved in methanol (35 mL) under nitrogen protection. Subsequently, a solution of di-tert-butyl dicarbonate (10.3 g, 47.0 mmol) in methanol (15 mL) was added slowly and dropwise. The reaction mixture was stirred overnight at room temperature. Upon completion of the reaction, the mixture was concentrated and the residue was dried under high vacuum to give 8.23 g (quantitative yield) of clear oily product. This oily product was dissolved in tetrahydrofuran (100 mL) and triethylamine (13.1 mL, 94.0 mmol) was added. Methanesulfonyl chloride (3.82 mL, 49.3 mmol) was added dropwise to this solution at 0 °C. After 1 h of reaction, the mixture was diluted with ethyl acetate and washed sequentially with 1 M aqueous hydrochloric acid, aqueous sodium bicarbonate and brine. The organic phase was dried with anhydrous sodium sulfate and concentrated to give 10.5 g (88% yield) of a clear oily product (compound 42.2), which solidified on standing. Electrospray mass spectrometry (ES(+)MS) showed m/e = 254 ([M+H]+).

References

[1] Journal of Organic Chemistry, 2000, vol. 65, # 20, p. 6368 - 6380
[2] Patent: US2006/35908, 2006, A1. Location in patent: Page/Page column 108
[3] Patent: US2015/197493, 2015, A1. Location in patent: Paragraph 0744; 0745; 0746
[4] Patent: WO2014/173928, 2014, A1. Location in patent: Page/Page column 52; 53
[5] Patent: WO2006/104356, 2006, A1. Location in patent: Page/Page column 27

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