Reaktion #1586752

Reaktionsgleichung

Pyridine

Dess-Martin periodinane

benzyl-3-[(tert-butoxycarbonyl)amino]-4-hydroxy-5-methylpiperidine-1-carboxylate

NaHCO3

Na2S2O3

→

sub-title compound

Ausbeute 95.0%

Benzyl-3-[(tert-butoxycarbonyl)amino]-5-methyl-4-oxopiperidine-1-carboxylate

Ausbeute 95.0%

Lösungsmittel

DCM

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONA solution containing
2. 2
   workup.ADDITIONwas added
3. 3
   workup.STIRRINGthe resulting mixture was stirred for 30 min
4. 4
   ExtraktionThe mixture was then extracted with DCM
5. 5
   TrocknenThe combined organic layers were dried over Na2SO4
6. 6
   Einengenconcentrated under reduced pressure
7. 7
   SonstigeThe resulting residue was purified by silica gel chromatography
8. 8
   Wascheneluting with 40% EtOAc in hexanes

Vorschrift

Pyridine (0.8 mL, 10 mmol) and Dess-Martin periodinane (1.8 g, 4.4 mmol) were added to a stirred solution of benzyl-3-[(tert-butoxycarbonyl)amino]-4-hydroxy-5-methylpiperidine-1-carboxylate (1.22 g, 3.35 mmol) in DCM (20 mL) at 0° C. The reaction mixture was stirred at room temperature for 16 h. A solution containing a mixture of NaHCO3 and Na2S2O3 was added and the resulting mixture was stirred for 30 min. The mixture was then extracted with DCM. The combined organic layers were dried over Na2SO4 and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography eluting with 40% EtOAc in hexanes to give the sub-title compound as a colorless oil (1.15 g, 95%). LCMS calc. for C19H26N2NaO5 (M+Na)+ m/z=385.2. found 385.0.

Quelle