Sulfuric Acid → HCID 14342016, compound

Following removal of the solvent under reduced pressure, the β-aminosulfate from the reaction of 1-(R)-cyclohexyl-l,2-cyclic sulfate (0.206 g, 1 mmol) and benzylamine (0.214 g, 2 mmol) was stirred with 20% H2SO4 (5 mL) and ether (5 mL) at room temperature (refluxing of the two phase mixture expedites the hydrolysis) for 12 hours. The organic phase was discarded and the aqueous phase was adjusted to pH 10 with 20% aq. NaOH and extracted with ether (3×20 mL). The combined organic phases were washed with brine (20 mL) and dried over Na2SO4. Concentration gave l(R)-cyclohexyl-2-benzylaminoethanol (0.117 g, 74%), mp. 56°-58° C., [α]22D=-1.2° (c 1, CHCI3 ; 1H NMR (CDCI3) δ 7.3 (S, 5 H), 3.75 (d, J 5.77 Hz, 2 H), 3.35 (m, 1 H), 2.75 (dd, J =2.5, 9.6 Hz, 2 H), 2.5 (dd, J 9.6, 13 Hz, 1 H), 1.9-1.5 (m, 5 H), 1.3-0.9 (m, 7 H).

1. customremoval of the solvent under reduced pressure
2. temperaturerefluxing of the two phase mixture
3. customthe hydrolysis) for 12 hours
4. extractionextracted with ether (3×20 mL)
5. washThe combined organic phases were washed with brine (20 mL)
6. dry with materialdried over Na2SO4
7. concentrationConcentration

ORD record

ord-cec794c06879473eb58392e58e2468bc

Source dataset

uspto-grants-1994_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05321143