反应详情

Sodium borohydride (4.4 mg, 0.12 mmol) followed by MeOH (0.2 mL) was added to a solution of {4-[(R)-2-oxo-6-(3-oxo-4-phenyl-butyl)-piperidin-1-yl]-but-2-ynyloxy}-acetic acid methyl ester (15 mg, 0.039 mmol) in CH2Cl2 (0.6 mL) at 0° C. After 5 min at 0° C. the reaction was quenched with aqueous HCl (0.2 M, 5 mL). The reaction mixture was extracted with CH2Cl2 (3×5 mL), then the combined extracts were dried (Na2SO4), filtered and concentrated in vacuo. Purification of the residue by flash column chromatography on silica gel (CH2Cl2→5% MeOH/CH2Cl2) afforded 13 mg (86%) of {4-[(R)-2-(3-hydroxy-4-phenyl-butyl)-6-oxo-piperidin-1-yl]-but-2-ynyloxy}-acetic acid methyl ester and 2 mg (14%) of (R)-1-[4-(2-hydroxy-ethoxy)-but-2-ynyl]-6-(3-hydroxy-4-phenyl-butyl)-piperidin-2-one.

1. customAfter 5 min at 0° C. the reaction was quenched with aqueous HCl (0.2 M, 5 mL)
2. extractionThe reaction mixture was extracted with CH2Cl2 (3×5 mL)
3. dry with materialthe combined extracts were dried (Na2SO4)
4. filtrationfiltered
5. concentrationconcentrated in vacuo
6. customPurification of the residue by flash column chromatography on silica gel (CH2Cl2→5% MeOH/CH2Cl2)