Diethyl Ether → (R)-4-(1-Aminoethyl)cyclohexan-1-ol

Tert-butyl(R)-1-(4-hydroxycyclohexyl)ethylcarbamate (4.49 g, 18.45 mmol) was dissolved in dichloromethane (25 mL) and cooled to 0° C. under nitrogen. HCl 2M in Ether (27.68 mL of 2 M, 55.35 mmol) was added and the reaction allowed to warm slowly to ambient temperature for 18 hours. The reaction mixture was concentrated in vacuo. The crude mixture was dissolved in MeOH (25 mL). MP-Carbonate was added (11.75 g, 36.90 mmol) and the reaction mixture was stirred for 3 hours. The resin was filtered and the mother liquors were concentrated to dryness to afford the title compound as an off white solid (2.39 g, 90% yield).

1. additionwas added
2. concentrationThe reaction mixture was concentrated in vacuo
3. dissolutionThe crude mixture was dissolved in MeOH (25 mL)
4. additionMP-Carbonate was added (11.75 g, 36.90 mmol)
5. filtrationThe resin was filtered
6. concentrationthe mother liquors were concentrated to dryness

ORD record

ord-dae4c4d4145c4bf890463e7421570468

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08962642B2