Reaktion #2343210

Reaktionsgleichung

sodium bicarbonate

triethylsilane

1-benzyloxycarbonyl-4-hydroxy-4-(2-methoxyphenyl)piperidine

trifluoroacetic acid

→

1-Benzyloxycarbonyl-4-(2-methoxyphenyl)piperidine

Lösungsmittel

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   ExtraktionThe bicarbonate solution was extracted with dichloromethane
2. 2
   TrocknenThe dichloromethane solution was dried
3. 3
   Sonstigeevaporated
4. 4
   Sonstigeto give the des-hydroxy compound (2.1 g)
5. 5
   SonstigeThis material was used in the next step without further purification

Vorschrift

A solution of 1-benzyloxycarbonyl-4-hydroxy-4-(2-methoxyphenyl)piperidine (2.59 g) in dichloromethane (45 mL) was treated with trifluoroacetic acid (8.6 g) followed by triethylsilane (17.5 g). The resulting brown reaction mixture was stirred for 5 minutes and then poured into a saturated solution of sodium bicarbonate. The bicarbonate solution was extracted with dichloromethane. The dichloromethane solution was dried and evaporated to give the des-hydroxy compound (2.1 g); NMR (CDCl3): 1.55-1.66 (m, 2), 1.78-1.82 (br, 2), 2.91, (m, 2), 3.11 (m, 1), 3.8 and 3.82 (s, 3), 4.32 (br, 2), 5.12-5.28 (m, 2), 6.84 (d, 4, J=9), 6.87-6.95 (m, 1), 7.11-7.25 (m, 2), 7.29-7.38 (m, 5); MS: m/z=326(M+1). This material was used in the next step without further purification.

Quelle