Dimethylformamide → Methyl 3-[4-(N-BOC-Piperidin-4-yl)butyloxy]isoxazole-5-carboxylate

HRID 1957581Notes

Reaction equation

HRID 1957581 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][CH2:16][CH2:17]I)[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C([O-])([O-])=O.[Cs+].[Cs+].[OH:25][C:26]1[CH:30]=[C:29]([C:31]([O:33][CH3:34])=[O:32])[O:28][N:27]=1.CN(C=O)C>CCOCC>[C:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][CH2:16][CH2:17][O:25][C:26]2[CH:30]=[C:29]([C:31]([O:33][CH3:34])=[O:32])[O:28][N:27]=2)[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 193480344-(N-BOC-Piperidin-4-yl)butyl iodideHCID 178498603HCID 178498603, compound

Product 1

HCID 19068162Methyl 3-[4-(N-BOC-Piperidin-4-yl)butyloxy]isoxazole-5-carboxylateYield 87.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 4-3 (3.0 g, 8.1 mmol), Cs2CO3 (2.6 g, 8.1 mmol), methyl 3-hydroxy-5-isoxazolecarboxylate (Aldrich) (1.2 g, 8.1 mmol), and DMF (20 mL) was stirred at ambient temperature for 20 h. The reaction mixture was diluted with ether and then washed with H2O and brine, dried (MgSO4), and concentrated. Flash chromatography (silica, 3% acetone/CH2Cl2) gave 4-4 (2.7 g) as a colorless solid. Rf 0.17 (silica, 3% acetone/CH2Cl2).

Workup

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

Sources & evidence

ORD record
ord-41880a4de2224318be61d23dfce8a42d
Source dataset
uspto-grants-1998_07
Patent number
US05786373

Reaction notes

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