Reaction #68807

Reaction equation

triphenylphosphine

di-tert-butyl azodicarboxylate

6-methoxy-pyridin-2-ol

(S)—N-{1-[4-(3-hydroxy-azetidin-1-yl)-phenyl]-ethyl}-acetamide

triphenylphosphine

di-tert-butyl azodicarboxylate

→

desired product

(S)—N-(1-{4-[3-(6-Methoxy-pyridin-2-yloxy)-azetidin-1-yl]-phenyl}-ethyl)-acetamide

Solvents

THF

THF

Conditions

Workup

1. 1
   workup.STIRRINGstirring
2. 2
   workup.WAITis continued for 2 h at 60° C
3. 3
   ConcentrationThe mixture is concentrated in vacuo
4. 4
   Otherthe residue is purified by HPLC (XBridge, acetronitrile/H2O (+0.1% NH4OH))

Procedure

To 13 mg (0.10 mmol) 6-methoxy-pyridin-2-ol in THF (1.0 mL) is added 23 mg (0.10 mmol) (S)—N-{1-[4-(3-hydroxy-azetidin-1-yl)-phenyl]-ethyl}-acetamide (V.1) in THF (1.0 mL). 29 mg (0.11 mmol) triphenylphosphine and 25 mg (0.11 mmol) di-tert-butyl azodicarboxylate are added and the mixture is stirred for 3 h at 60° C. Another portion of 29 mg (0.11 mmol) triphenylphosphine and 25 mg (0.11 mmol) di-tert-butyl azodicarboxylate are added and stirring is continued for 2 h at 60° C. The mixture is concentrated in vacuo and the residue is purified by HPLC (XBridge, acetronitrile/H2O (+0.1% NH4OH)) to yield the desired product.

Source