Reaktion #1137684

Reaktionsgleichung

DIAD

1-hydroxyisoquinoline

(S)-1-BOC-3-hydroxypiperidine

Ph3P

→

(R)-tert-butyl 3-(isoquinolin-1-yloxy)piperidine-1-carboxylate

Lösungsmittel

EtOAc

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGThe mixture was stirred at RT for 1 h
2. 2
   Waschenwashed with water ×3
3. 3
   Sonstigedried
4. 4
   Einengenconcentrated in vacuo

Vorschrift

A mixture of 1-hydroxyisoquinoline (1.00 g, 6.9 mmol), (S)-1-BOC-3-hydroxypiperidine (4.17 g, 20.7 mmol), Ph3P (7.23 g, 27.6 mmol) in THF (40 mL) was stirred at RT into a clear solution. DIAD (5.43 mL, 27.6 mmol) was added dropwise. The mixture was stirred at RT for 1 h and then at 50° C. for overnight. The mixture was diluted with EtOAc, washed with water ×3, dried, and concentrated in vacuo. The residue was subjected to flash column chromatography with 0% to 15% EtOAc in DCM to afford (R)-tert-butyl 3-(isoquinolin-1-yloxy)piperidine-1-carboxylate (53).

Quelle