(3-HYDROXY-CYCLOHEXYL)-CARBAMIC ACID TERT-BUTYL ESTER Chemical Properties

Boiling point:

337.7±31.0 °C(Predicted)

Density 

1.06

storage temp. 

2-8°C

pka

12.32±0.40(Predicted)

Appearance

White to off-white Solid

Safety Information

Hazard Codes 

Xn,N

Risk Statements 

22-50/53

Safety Statements 

60-61

(3-HYDROXY-CYCLOHEXYL)-CARBAMIC ACID TERT-BUTYL ESTER Usage And Synthesis

Synthesis

The general procedure for the synthesis of tert-butyl 3-hydroxycyclohexylcarbamate from N-Boc-3-cyclohexanone amine was as follows: sodium borohydride (710 mg, 18.8 mmol, 2.0 eq.) was slowly added to a solution of tert-butyl 3-oxocyclohexylcarbamate (2.0 g, 9.38 mmol, 1.0 eq.) dissolved in methanol (20 mL) at 0 °C. The reaction mixture was stirred continuously for 14 hours at room temperature. Upon completion of the reaction, the reaction was quenched with deionized water (20 mL) followed by extraction with ethyl acetate (30 mL x 3). The organic phases were combined, dried with anhydrous sodium sulfate and concentrated under reduced pressure to afford the target product tert-butyl 3-hydroxycyclohexylcarbamate (2.0 g, yield: 100%).

References

[1] Patent: US2016/200730, 2016, A1. Location in patent: Paragraph 0484; 0485
[2] Patent: WO2015/39348, 2015, A1. Location in patent: Page/Page column 34

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