Triphenylphosphine → 6-(1-Isopropyl-piperidin-4-yloxy)-benzo[b]thiophene-2-carboxylic acid ethyl ester

HRID 493184Notes

Reaction equation

HRID 493184 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]2[CH:11]=[C:12]([OH:15])[CH:13]=[CH:14][C:8]=2[CH:7]=1)=[O:5])[CH3:2].[CH:16]([N:19]1[CH2:24][CH2:23][CH:22](O)[CH2:21][CH2:20]1)([CH3:18])[CH3:17].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]2[CH:11]=[C:12]([O:15][CH:22]3[CH2:23][CH2:24][N:19]([CH:16]([CH3:18])[CH3:17])[CH2:20][CH2:21]3)[CH:13]=[CH:14][C:8]=2[CH:7]=1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 796811-Isopropylpiperidin-4-olHCID 5363146Diisopropyl azodicarboxylateHCID 58047243Ethyl 6-hydroxybenzo[b]thiophene-2-carboxylate

Product 1

HCID 687272376-(1-Isopropyl-piperidin-4-yloxy)-benzo[b]thiophene-2-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 6-hydroxy-benzo[b]thiophene-2-carboxylic acid ethyl ester (0.300 g, 1.35 mmol, prepared as described above, but using ethyl instead of methyl thioglycolate), dissolved in 13.5 mL of THF, was added successively at 10° C. 1-isopropyl-piperidin-4-ol (0.387 g, 2 eq.), triphenylphosphine (0.708 g, 2 eq.) and DIAD (0.530 mL, 2 eq.), and the mixture then kept at this temperature for another 2 h. Pouring onto crashed ice, twofold extraction with AcOEt, washing with water and brine, drying over magnesium sulfate, and evaporation of all solvents, followed by flash chromatography (SiO2, MeOH/AcOEt=1/9), delivered 0.360 g of the title compound as off-white solid.

Workup

  1. additionwas added successively at 10° C
  2. additionPouring
  3. extractionice, twofold extraction with AcOEt
  4. washwashing with water and brine
  5. dry with materialdrying over magnesium sulfate, and evaporation of all solvents

Sources & evidence

ORD record
ord-645bac8a1173438d86a0d87444e5dca2
Source dataset
uspto-grants-2009_05
Patent number
US07534788B2

Reaction notes

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