Carbamic acid, (3-hydroxy-2,2-dimethylpropyl)-, 1,1-dimethylethyl ester (9CI) Chemical Properties

Boiling point:

311.0±25.0 °C(Predicted)

Density 

0.998±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

pka

12.67±0.46(Predicted)

Appearance

White to off-white Solid

Carbamic acid, (3-hydroxy-2,2-dimethylpropyl)-, 1,1-dimethylethyl ester (9CI) Usage And Synthesis

Synthesis

Step 1: Synthesis of tert-butyl (3-hydroxy-2,2-dimethylpropyl) carbamate: 3-amino-2,2-dimethyl-1-propanol (1.50 g, 14.5 mmol) was dissolved in dichloromethane (70 ml) followed by addition of di-tert-butyl dicarbonate (3.49 g, 16.0 mmol). The reaction mixture was stirred at room temperature for 16 hours. After completion of the reaction, saturated ammonium chloride solution (NH4Cl) was added and stirring was continued for 10 minutes. The organic and aqueous layers were separated, and the organic phase was washed with saturated sodium bicarbonate solution (NaHCO3), dried over anhydrous sodium sulfate (Na2SO4), and concentrated under reduced pressure to afford the target product, 2,2-dimethyl-3-(Boc-amino)-1-propanol, as a white solid (3.40 g, quantitative yield).The LC-MS analysis showed the molecular ion peak as 226.20 (M + Na+).

References

[1] Patent: WO2011/71725, 2011, A1. Location in patent: Page/Page column 53
[2] ChemMedChem, 2014, vol. 9, # 1, p. 197 - 206
[3] Patent: WO2006/57868, 2006, A1. Location in patent: Page/Page column 72
[4] Patent: WO2018/109648, 2018, A1. Location in patent: Page/Page column 52; 56
[5] Patent: US2005/54701, 2005, A1

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