Trifluoroacetic acid → 6'-Morpholino-1',2,2',3,5,6-hexahydrospiro[pyran-4,3'-pyrrolo[3,2-b]pyridine]

To a stirred solution of tert-butyl 6′-morpholino-2,3,5,6-tetrahydrospiro[pyran-4,3′-pyrrolo[3,2-b]pyridine]-1′(2′H)-carboxylate (5.8 g, 15.45 mmol) in DCM (30 mL) was added TFA (23.80 mL, 309 mmol) and the reaction was stirred at rt for 3 h. After this time the reaction was evaporated under reduced pressure and dried under vacuum overnight. After this time the reaction was partitioned between EtOAc (80 mL) and 1.0M aqueous HCl (200 mL). The separated aqueous layer was washed with EtOAc (40 mL). The aqueous layer was then basified to pH 14 with aqueous NaOH and extracted with EtOAc (2×200 mL) and DCM (100 mL). The combined organic layers were dried over MgSO4, filtered and evaporated in vacuo to give 6′-morpholino-1′,2,2′,3,5,6-hexahydrospiro[pyran-4,3′-pyrrolo[3,2-b]pyridine] as a white solid. Mass Spectrum (ESI) m/e=276.2 (M+1)

1. customAfter this time the reaction was evaporated under reduced pressure
2. customdried under vacuum overnight
3. customAfter this time the reaction was partitioned between EtOAc (80 mL) and 1.0M aqueous HCl (200 mL)
4. washThe separated aqueous layer was washed with EtOAc (40 mL)
5. extractionextracted with EtOAc (2×200 mL) and DCM (100 mL)
6. dry with materialThe combined organic layers were dried over MgSO4
7. filtrationfiltered
8. customevaporated in vacuo

ORD record

ord-346c958146fb4ffb81a4e85182b82d17

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08765940B2