Acetic Acid → HCID 66592127, compound

(1S,4S)-(−)-2,5-diazabicyclo[2.2.1]heptan-5-ylcarboxylic acid tert-butyl ester (3.00 g, 15.13 mmol) and [(1-ethoxycyclopropyl)oxy]trimethylsilane (3.96 g, 22.70 mmol) were dissolved in methanol (30 mL), and while stirring the solution at room temperature, acetic acid (0.87 mL, 5.13 mmol) and then sodium cyanoborohydride (1.06 g, 15.13 mmol) were added thereto. Then, the mixture was heated to reflux for 21 hours. The reaction liquor was left to cool naturally, then a saturated aqueous solution of sodium hydrogen carbonate (100 mL) was added thereto, and the mixture was extracted with ethyl acetate (200 mL). The extract was washed with saturated brine (100 mL), and then dried over anhydrous sodium sulfate, and then the solvent was concentrated under reduced pressure. The obtained residue was purified by column chromatography using silica gel [chloroform-methanol (10:1)], to obtain the title compound (3.61 g, 100%) as an oily matter.

1. temperatureThen, the mixture was heated
2. temperatureto reflux for 21 hours
3. waitThe reaction liquor was left
4. temperatureto cool naturally
5. extractionthe mixture was extracted with ethyl acetate (200 mL)
6. washThe extract was washed with saturated brine (100 mL)
7. dry with materialdried over anhydrous sodium sulfate
8. concentrationthe solvent was concentrated under reduced pressure
9. customThe obtained residue was purified by column chromatography

ORD record

ord-27f3c938abe34e89afc0a0668f74b019

Source dataset

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08129366B2