Sodium hydride → Benzyl [(9S)-11-oxo-9-phenyl-6,10-diazaspiro[4.6]undec-10-yl]acetate

To a suspension of sodium hydride (0.147 g, 6.14 mmol) in THF (10 mL) was added (9S)-9-phenyl-6,10-diazaspiro[4.6]undecan-11-one (0.300 g, 1.23 mmol) at ambient temperature. The reaction was warmed to 60° C. for 2 h, then cooled to ambient temperature. Benzyl bromoacetate (0.309 g, 1.35 mmol) was added dropwise to the reaction. After 1 h, the mixture was quenched with a saturated aqueous ammonium chloride solution. The mixture was concentrated in vacuo then partitioned between H2O and CH2Cl2. The aqueous phase was then extracted several times with CH2Cl2. The combined organic extracts were washed with saturated brine, then dried over MgSO4, filtered and concentrated in vacuo The residue was purified by silica gel chromatography, eluting with a gradient of EtOAc:hexane—0:100 to 100:0, to yield the title compound. MS: m/z=393 (M+1).

1. temperaturecooled to ambient temperature
2. customthe mixture was quenched with a saturated aqueous ammonium chloride solution
3. concentrationThe mixture was concentrated in vacuo
4. customthen partitioned between H2O and CH2Cl2
5. extractionThe aqueous phase was then extracted several times with CH2Cl2
6. washThe combined organic extracts were washed with saturated brine
7. dry with materialdried over MgSO4
8. filtrationfiltered
9. concentrationconcentrated in vacuo The residue
10. customwas purified by silica gel chromatography
11. washeluting with a gradient of EtOAc

ORD-Eintrag

ord-e695c8738f0e44a9a608df5c65091e2e

Quelldatensatz

uspto-grants-2009_12

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07629338B2