Hydrochloric Acid → 4-Allyl-4-amino-cyclohexanol

The crude 1-allyl-4-(tert-butyl-dimethyl-silanyloxy)-cyclohexylamine (16, step a) was dissolved in 100 mL of diethyl ether. Then, 100 mL of 1N aqueous HCl were added dropwise and the resultant biphasic mixture was stirred for 30 min. The layers were separated, the aqueous layer was washed with diethyl ether and the pH adjusted to pH8 by the addition of solid sodium hydroxide. The suspension was then extracted with a 3:1 mixture of dichloromethane and 2-propanol and the combined organic extracts were concentrated in vacuo to afford 0.54 g of the title compound as mixture of diastereomers (1.5:1). Rt=0.15 min, 0.27 min (Method C). Detected mass: 156.2 (M+H+).

1. customThe layers were separated
2. washthe aqueous layer was washed with diethyl ether
3. additionthe pH adjusted to pH8 by the addition of solid sodium hydroxide
4. extractionThe suspension was then extracted with a 3:1 mixture of dichloromethane and 2-propanol
5. concentrationthe combined organic extracts were concentrated in vacuo

ORD record

ord-3fc7a854a3c94876bc4104bdec93a589

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08710077B2