Water → 2-Oxa-8-azaspiro[4.5]decan-4-ol;hydrochloride

Methanesulfonyl chloride (173 μL, 2.2 mmol) in dichloromethane (100 mL) was added dropwise to a solution of (RS)-1,1-dimethylethyl 4-hydroxymethyl-4-(1,2-dihydroxyethyl)-1-piperidinecarboxylate (Description 98, 615 mg, 2.2 mmol) and triethylamine (933 μL, 6.6 mmol) in dichloromethane (150 mL) and the mixture was stirred at room temperature for 16 hours. Water (100 mL) was added and the layers were separated. The aqueous fraction was extracted with dichloromethane (2×100 mL), the combined organic fractions were dried (MgSO4) and the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel, eluting with isohexane/EtOAc (50:50) and the residue was suspended in diethyl ether (50 mL) and treated with methanolic hydrogen chloride (0.25M, 3 mL). The mixture was stirred at room temperature for 30 minutes, then the solvent was evaporated under reduced pressure to give the title compound as a solid (150 mg, 35%). m/z (ES+) 158 (M+1).

1. customthe layers were separated
2. extractionThe aqueous fraction was extracted with dichloromethane (2×100 mL)
3. dry with materialthe combined organic fractions were dried (MgSO4)
4. customthe solvent was evaporated under reduced pressure
5. customThe residue was purified by flash column chromatography on silica gel
6. washeluting with isohexane/EtOAc (50:50)
7. additiontreated with methanolic hydrogen chloride (0.25M, 3 mL)
8. stirringThe mixture was stirred at room temperature for 30 minutes
9. customthe solvent was evaporated under reduced pressure

ORD record

ord-0b6508f8b5404813865ba6a17161d1dd

Source dataset

uspto-grants-2006_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07105507B2