Triethylamine → HCID 58745550, compound

To a stirred mixture of trans-tert-butyl 4-amino-3-hydroxypiperidine-1-carboxylate (1.05 g, 4.86 mmol) in 80 mL of dichloromethane was added triethylamine (5.89 g, 5.83 mmol), followed by the addition of N-(benzyloxycarbonyloxy)succinimide (1.27 g, 5.10 mmol) at 0° C. The reaction mixture was stirred at room temperature for 16 hours and then diluted with 100 mL of dichloromethane. The solution mixture was washed with 5% citric acid solution (2×100 mL), 5% potassium carbonate solution (2×100 mL) and brine (200 mL). The organic layer was dried over anhydrous sodium sulfate and filtered, followed by concentration under reduced pressure. The resultant oily matter was purified by silica gel column chromatography (ethyl acetate: petroleum ether=1:4˜1:2) to afford the title compound (1.7 g, ˜100%, crude) as a colorless oil. MS (ES+) C18H26N2O5 requires: 350, found: 251 [M+H−100]+.

1. washThe solution mixture was washed with 5% citric acid solution (2×100 mL), 5% potassium carbonate solution (2×100 mL) and brine (200 mL)
2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
3. filtrationfiltered
4. concentrationfollowed by concentration under reduced pressure
5. customThe resultant oily matter was purified by silica gel column chromatography (ethyl acetate: petroleum ether=1:4˜1:2)

ORD record

ord-4a8ceae232aa4583adc3b721b5ef21a6

Source dataset

uspto-grants-2016_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09434700B2