Propargyl bromide → Methyl 2-propargyloxy-4-(N-t-butyloxycarbonyl-4-piperidinyloxy)benzoate

HRID 1377723Notes

Reaction equation

HRID 1377723 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]([O:12][CH:13]2[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]2)[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[CH2:26](Br)[C:27]#[CH:28].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[CH2:28]([O:1][C:2]1[CH:11]=[C:10]([O:12][CH:13]2[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]2)[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5])[C:27]#[CH:26]

Participants

5

Reactant 3

HCID 7842Propargyl bromideHCID 10796Cesium carbonateHCID 105940774-(N-t-Butoxycarbonyl-4-piperidinyloxy)-2-hydroxybenzoic acid methyl ester

Product 1

HCID 22914696Methyl 2-propargyloxy-4-(N-t-butyloxycarbonyl-4-piperidinyloxy)benzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl 2-hydroxy-4-(N-t-butyloxycarbonyl-4-piperidinyloxy)benzoate (0.5 gm, 1.42 mmol) from Step 1 of Example 25 was dissolved in DMF (5 mL) and propargyl bromide (186 mg, 1.56 mmol) was added followed by cesium carbonate (925 mg, 2 eq.) and the mixture was stirred 16 hrs. The solids were removed by filtration and the filtrate solvents were removed under reduced pressure. The residue was purified by pressurized silica gel column chromatography using 1:1 ethyl acetate:hexanes as eluant. Methyl 2-propargyloxy-4-(N-t-butyloxycarbonyl-4-piperidinyloxy)benzoate was obtained as a gum.

Workup

  1. customThe solids were removed by filtration
  2. customthe filtrate solvents were removed under reduced pressure
  3. customThe residue was purified by pressurized silica gel column chromatography

Sources & evidence

ORD record
ord-a37e663377f94bb0a598daf7cfaf81c3
Source dataset
uspto-grants-1997_09
Patent number
US05665719

Reaction notes

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