Dimethylformamide → HCID 19068171, compound

HRID 1957576Notes

Reaction equation

HRID 1957576 reaction equation
[OH:1][C:2]1[CH:6]=[C:5]([C:7]([O:9][CH3:10])=[O:8])[O:4][N:3]=1.[C:11]([N:18]1[CH2:23][CH2:22][CH:21]([CH2:24][CH2:25][CH2:26]I)[CH2:20][CH2:19]1)([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12].C([O-])([O-])=O.[Cs+].[Cs+].CN(C=O)C>CCOCC>[C:11]([N:18]1[CH2:19][CH2:20][CH:21]([CH2:24][CH2:25][CH2:26][O:1][C:2]2[CH:6]=[C:5]([C:7]([O:9][CH3:10])=[O:8])[O:4][N:3]=2)[CH2:22][CH2:23]1)([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 9975355Tert-butyl 4-(3-iodopropyl)piperidine-1-carboxylateHCID 178498603HCID 178498603, compound

Product 1

HCID 19068171HCID 19068171, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of methyl 3-hydroxy-5-isoxazolecarboxylate (Aldrich) (3-5) (286 mg, 2.0 mmol), 3-4 (706 mg, 2.0 mmol), Cs2CO3 (650 mg, 2.0 mmol), and DMF (10 mL) was stirred at ambient temperature. After 72 hours the reaction mixture was diluted with ether and then washed with H2O and brine, dried (MgSO4), and concentrated. Flash chromatography (silica, 4% acetone/CH2Cl2) gave 3-6 as a colorless solid. Rf 0.54 (silica, 40 %EtOAc/hexanes).

Workup

  1. washwashed with H2O and brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-18110f652a764c16bd5b52672752c62f
Source dataset
uspto-grants-1998_07
Patent number
US05786373

Reaction notes

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