Sodium hydride → HCID 45786893, compound

A suspension of pre-washed NaH (0.1 g, 2.48 mmol, 60% percent dispersion in mineral oil) in THF (2 mL) was added to an ice cold solution of 4-hydroxy-piperidine-1-carboxylic acid tert-butyl ester (0.5 g, 2.48 mmol) in dry THF (3 mL). The mixture was stirred for 20 minutes, and added to 2-chloro-5-nitro-pyridine (0.36 g, 2.26 mmol) in portions. After the addition was completed, the cooling bath was removed and the reaction mixture was stirred at 22° C. overnight. The reaction mixture was cooled in an ice bath and treated with a saturated aqueous sodium bicarbonate solution (5 mL). The reaction mixture was diluted with ethyl acetate (25 mL) and distilled water (25 mL). The separated aqueous phase was extracted with ethyl acetate (3×35 mL), and the combined organic phases were dried over sodium sulfate, filtered and concentrated under reduced pressure. Chromatography provided the title compound.

1. additionAfter the addition
2. customthe cooling bath was removed
3. stirringthe reaction mixture was stirred at 22° C. overnight
4. temperatureThe reaction mixture was cooled in an ice bath
5. additiontreated with a saturated aqueous sodium bicarbonate solution (5 mL)
6. additionThe reaction mixture was diluted with ethyl acetate (25 mL)
7. distillationdistilled water (25 mL)
8. extractionThe separated aqueous phase was extracted with ethyl acetate (3×35 mL)
9. dry with materialthe combined organic phases were dried over sodium sulfate
10. filtrationfiltered
11. concentrationconcentrated under reduced pressure

ORD record

ord-0efa48c485c74abb9af80f179a094573

Source dataset

uspto-grants-2016_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09302989B2