(4-HYDROXYMETHYL-BENZYL)-CARBAMIC ACID TERT-BUTYL ESTER Chemical Properties

Melting point:

98 °C

Boiling point:

397.2±30.0 °C(Predicted)

Density 

1.106±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

form 

solid

pka

12.19±0.46(Predicted)

color 

White

Safety Information

Hazard Codes 

Xi

Hazard Note 

Irritant

HS Code 

2906290090

(4-HYDROXYMETHYL-BENZYL)-CARBAMIC ACID TERT-BUTYL ESTER Usage And Synthesis

Synthesis

GENERAL STEPS: A mixture of 4-(aminomethyl)benzenemethanol (1 g, 7.29 mmol) and di-tert-butyl dicarbonate (1.59 g, 7.29 mmol) in dichloromethane (30 mL) was reacted at room temperature with stirring overnight. Upon completion of the reaction, the reaction mixture was concentrated under reduced pressure to remove the solvent. The crude product was purified by silica gel column chromatography with the eluent being a solvent mixture of dichloromethane and ethyl acetate (1:1, v/v) to afford tert-butyl 4-(hydroxymethyl)benzylcarbamate (0.8 g, 2.28 mmol, 31% yield) as a white solid. The product was characterized by 1H NMR (400 MHz, DMSO-d6): δ 7.37 (s, 1H), 7.22 (dd, J = 27.8, 8.0 Hz, 4H), 5.13 (t, J = 5.7 Hz, 1H), 4.46 (d, J = 5.7 Hz, 2H), 4.10 (d, J = 6.1 Hz, 2H), 1.36 (s, 9H ).

References

[1] Patent: WO2006/12135, 2006, A1. Location in patent: Page/Page column 49-51
[2] Patent: US2006/293379, 2006, A1. Location in patent: Page/Page column 63
[3] Angewandte Chemie - International Edition, 2012, vol. 51, # 4, p. 941 - 944
[4] Chemical Communications, 2010, vol. 46, # 7, p. 1073 - 1075
[5] Journal of Medicinal Chemistry, 2009, vol. 52, # 1, p. 33 - 47

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