Diisopropyl Ether → HCID 21952873, compound

HRID 2115254Notes

Reaction equation

[N+:1](=[CH:3][CH2:4][O:5][C:6]([CH2:8][C:9]1(O)[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]1)=[O:7])=[N-:2].O(C(C)C)C(C)C.O=P(Cl)(Cl)Cl.[OH-].[Na+]>N1C=CC=CC=1>[N+:1](=[CH:3][CH2:4][O:5][C:6]([CH2:8][C:9]1[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH:10]=1)=[O:7])=[N-:2]

Participants

Conditions

Temperature: -10 °C

Procedure

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.

Workup

waitThe mixture is then left
extractionis then extracted 3 times with EtOAc
washThe organic phase is washed with a saturated NaCl solution
dry with materialdried over MgSO4
customThe hydrated salt is removed by filtration
concentrationthe dry filtrate is concentrated under reduced pressure to 1/10 of its initial volume
customRT=4.57

Sources & evidence

ORD record: ord-65a112ab94ee4b8eaaa2ba4de5900a3e
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07435820B2

Reaction notes

Loading…