Diisopropyl Ether → HCID 21952873, compound

Participants

Reaction Conditions

Reaction Steps

78.0 ml of dry pyridine are added to a solution of 15.12 g of tert-butyl 4-(diazoethoxycarbonylmethyl)-4-hydroxypiperidine-1-carboxylate into 250 ml of iPr2O. The mixture is cooled to −10° C. and 8.86 ml of POCl3 are added slowly with vigorous stirring. The mixture is then left to return to ambient temperature for 12 hours with stirring. The reaction mixture is decomposed with 500 ml of a 0.1 M NaOH solution, and is then extracted 3 times with EtOAc. The organic phase is washed with a saturated NaCl solution and dried over MgSO4. The hydrated salt is removed by filtration and the dry filtrate is concentrated under reduced pressure to 1/10 of its initial volume. LC/MS: RT=4.57; [M+1]+=296.31 The product is used as it is for the subsequent step.

Provenance & Evidence