Reaktion #495132

Reaktionsgleichung

(R)-tert-butyl-4-(3-(methylsulfonyloxy)-2-oxopyrrolidin-1-yl)piperidine-1-carboxylate

4-(5-methyl-1H-tetrazol-1-yl)phenol

K2CO3

→

tert-butyl-4-(3-(4-(5-methyl-1H-tetrazol-1-yl)phenoxy)-2-oxopyrrolidin-1-yl)piperidine-1-carboxylate

Ausbeute 52.0%

Lösungsmittel

water

EtOAc

DMSO

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe organic layer was separated
2. 2
   Extraktionthe aqueous layer extracted with EtOAc (2×15 mL)
3. 3
   TrocknenThe combined organic layers were dried with MgSO4
4. 4
   Einengenconcentrated in vacuo
5. 5
   SonstigeThe material was purified by silica gel chromatography
6. 6
   Wascheneluting with 1:1 hexanes/EtOAc to EtOAc

Vorschrift

To a solution of (R)-tert-butyl-4-(3-(methylsulfonyloxy)-2-oxopyrrolidin-1-yl)piperidine-1-carboxylate (Preparation D; 1.03 g, 2.84 mmol) and 4-(5-methyl-1H-tetrazol-1-yl)phenol (500 mg, 2.84 mmol) in DMSO (10 mL) was added K2CO3 (1.18 g, 8.51 mmol). The reaction was heated to 70° C. for 12 hours and then diluted with water (10 mL) and EtOAc (10 mL). The organic layer was separated and the aqueous layer extracted with EtOAc (2×15 mL). The combined organic layers were dried with MgSO4 and concentrated in vacuo. The material was purified by silica gel chromatography eluting with 1:1 hexanes/EtOAc to EtOAc to yield tert-butyl-4-(3-(4-(5-methyl-1H-tetrazol-1-yl)phenoxy)-2-oxopyrrolidin-1-yl)piperidine-1-carboxylate (621 mg, 52%) as an off white solid.

Quelle