Water → HCID 58980888, compound
Reaction equation
[C:1]([N:8]1[CH2:15][C@@H:14]([F:16])[CH2:13][C@H:9]1[C:10](O)=[O:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].O.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1>[F:16][C@@H:14]1[CH2:15][N:8]([C:1]([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2])[C@H:9]([CH2:10][OH:11])[CH2:13]1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
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%