Cyclohexanol → HCID 13240890, compound

620 mg (4.80 mmol) of ethyl isocyanatoacetate was dissolved in 5 ml of dichloromethane. 10 ml of a solution of 0.56 ml (5.28 mmol) of cyclohexanol in 10 ml of dichloromethane was added to the obtained solution under cooling with ice, and they were stirred at room temperature for 15 minutes. The reaction mixture was concentrated under reduced pressure. 5.8 ml of 1 N aqueous lithium hydroxide solution was added to the concentrate, and the obtained mixture was stirred in a solvent mixture of methanol:water=2:1 at room temperature for 2 hours. The reaction mixture was concentrated under reduced pressure. Water was added to the concentrate and the resultant aqueous layer was washed with ethyl acetate. 0.1 N aqueous hydrochloric acid solution was added to the aqueous layer to control pH at 2 to 3. After extracting with ethyl acetate, the organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure to obtain the title compound.

1. temperatureunder cooling with ice, and they
2. concentrationThe reaction mixture was concentrated under reduced pressure
3. addition5.8 ml of 1 N aqueous lithium hydroxide solution was added to the concentrate
4. stirringthe obtained mixture was stirred in a solvent mixture of methanol
5. waitwater=2:1 at room temperature for 2 hours
6. concentrationThe reaction mixture was concentrated under reduced pressure
7. additionWater was added to the
8. concentrationconcentrate
9. washthe resultant aqueous layer was washed with ethyl acetate
10. addition0.1 N aqueous hydrochloric acid solution was added to the aqueous layer
11. extractionAfter extracting with ethyl acetate
12. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
13. concentrationconcentrated under reduced pressure

ORD record

ord-60f0c9302d574741a82a19ab8461c926

Source dataset

uspto-grants-2008_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07462630B2