Water → HCID 58980888, compound

N-Boc-cis-4-fluoro-L-proline (2 g, 8.575 mmol) was dissolved in tetrahydrofuran (20 ml), the solution was cooled and boron hydride-tetrahydrofuran complex (1 mol/l, 12.86 ml) was added slowly at 0° C. The reaction mixture warmed slowly to room temperature, after stirring for 3 h it was cooled again to 0° C., water (5 ml) was slowly added dropwise, potassium carbonate (2 g, 14.477 mmol) was added and the mixture was stirred for 30 min. After separation of the phases, the aqueous phase was extracted with diethyl ether (3×20 ml) and the combined organic phases were dried over sodium sulfate and concentrated in vacuo. The crude product was purified by column chromatography (silica gel) with diethyl ether/hexane (4:1). Yield: 1.73 g, 92%

1. temperaturethe solution was cooled
2. additionboron hydride-tetrahydrofuran complex (1 mol/l, 12.86 ml) was added slowly at 0° C
3. temperaturewas cooled again to 0° C.
4. stirringthe mixture was stirred for 30 min
5. customAfter separation of the phases
6. extractionthe aqueous phase was extracted with diethyl ether (3×20 ml)
7. dry with materialthe combined organic phases were dried over sodium sulfate
8. concentrationconcentrated in vacuo
9. customThe crude product was purified by column chromatography (silica gel) with diethyl ether/hexane (4:1)

ORD record

ord-b24e5f897a914be991b93b5b3542faa1

Source dataset

uspto-grants-2012_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08119805B2