(4-OXO-4-PHENYL-BUTYL)-CARBAMIC ACID TERT-BUTYL ESTER Chemical Properties

Melting point:

90-91°C

Boiling point:

406.8±28.0 °C(Predicted)

Density 

1.058±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

pka

12.66±0.46(Predicted)

Appearance

White to pink Solid

(4-OXO-4-PHENYL-BUTYL)-CARBAMIC ACID TERT-BUTYL ESTER Usage And Synthesis

Synthesis

Step A: Preparation of tert-butyl N-(4-oxo-4-phenylbutyl)carbamate: tert-butyl 2-oxo-pyrrolidine-1-carboxylate (7.03 g, 38 mmol) was dissolved in tetrahydrofuran (130 mL) and cooled to -78°C. Phenylmagnesium bromide (1.0 M solution, 50 mL) was slowly added at -78 °C. The reaction mixture was stirred at -78 °C for 2 h before the reaction was quenched with 2 M hydrochloric acid solution (35 mL). Subsequently, the reaction mixture was slowly warmed to room temperature and the aqueous layer was extracted with ethyl acetate (2 x 100 mL). The organic phases were combined, washed with saturated brine (50 mL), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give 9.56 g of the title compound in 96% yield.

References

[1] Patent: WO2006/44825, 2006, A2. Location in patent: Page/Page column 55
[2] Patent: US2012/184542, 2012, A1. Location in patent: Page/Page column 109
[3] Organic Letters, 2011, vol. 13, # 16, p. 4348 - 4351

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