Reaktion #1586751

Reaktionsgleichung

Benzyl-(3R,4R,5S)-3-[(tert-butoxycarbonyl)amino]-5-methyl-4-(1,1,2,2-tetramethylpropoxy)piperidine-1-carboxylate

tetra-n-butylammonium fluoride

→

sub-title compound

Ausbeute 100.0%

Benzyl-(3R,4R,5S)-3-[(tert-butoxycarbonyl)amino]-4-hydroxy-5-methylpiperidine-1-carboxylate

Ausbeute 100.0%

Lösungsmittel

THF

THF

EtOAc

Reaktionsbedingungen

Aufarbeitung

1. 1
   WaschenThe mixture was washed 2 times with brine
2. 2
   Sonstigedried
3. 3
   Einengenconcentrated under reduced pressure
4. 4
   SonstigeThe crude product was purified by silica gel chromatography
5. 5
   Wascheneluting with 25-75% EtOAc in hexanes

Vorschrift

Benzyl-(3R,4R,5S)-3-[(tert-butoxycarbonyl)amino]-5-methyl-4-(1,1,2,2-tetramethylpropoxy)piperidine-1-carboxylate (1.88 g, 4.06 mmol) was dissolved in THF (20 mL) and a 1.0 M solution of tetra-n-butylammonium fluoride in THF (4.7 mL, 4.7 mmol) was added. The reaction mixture was stirred for 30 min. at room temperature and then diluted with EtOAc. The mixture was washed 2 times with brine, then dried and concentrated under reduced pressure. The crude product was purified by silica gel chromatography eluting with 25-75% EtOAc in hexanes to give the sub-title compound as a white solid (1.48 g, 82%). LCMS calc. for C19H28N2NaO5 (M+Na)+ m/z=387.2. found 387.0.

Quelle