Acetic Acid → (S)-tert-butyl 3-(piperidin-1-ylmethyl)piperidine-1-carboxylate
Reaktionsgleichung
[CH:1]([C@@H:3]1[CH2:8][CH2:7][CH2:6][N:5]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:4]1)=O.[NH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].CC(O)=O>>[N:16]1([CH2:1][C@@H:3]2[CH2:8][CH2:7][CH2:6][N:5]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:4]2)[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1Komponenten
5
Versuchsvorschrift
To a solution of (R)-tert-butyl 3-formylpiperidine-1-carboxylate (110 mg, 0.51 mmol) and piperidine (53 mg, 0.62 mmol) was added NaBH(OAc)3 (153 mg, 0.73 mmol) and AcOH (37.2 mg, 35 μL, 0.62 mmol) at room temperature. The mixture was stirred for 8 h at the room temperature. The reaction was quenched by pouring into 20 mL 5% aqueous NaOH and diluted with ethylacetate. The mixture was extracted with ethyl acetate (3×15 mL) and the combined organic layers washed with brine (2×10 mL) and dried over Na2SO4. The mixture was concentrated under reduced pressure and the crude product was used directly in the next reaction without further purification.