Triphenylphosphine → 5-(1-Isopropyl-piperidin-4-yloxy)-benzo[b]thiophene-2-carboxylic acid methyl ester

HRID 493179Notes

Reaction equation

HRID 493179 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:9][C:8]2[CH:10]=[CH:11][C:12]([OH:14])=[CH:13][C:7]=2[CH:6]=1)=[O:4].[CH:15]([N:18]1[CH2:23][CH2:22][CH:21](O)[CH2:20][CH2:19]1)([CH3:17])[CH3:16].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>[CH3:1][O:2][C:3]([C:5]1[S:9][C:8]2[CH:10]=[CH:11][C:12]([O:14][CH:21]3[CH2:22][CH2:23][N:18]([CH:15]([CH3:17])[CH3:16])[CH2:19][CH2:20]3)=[CH:13][C:7]=2[CH:6]=1)=[O:4]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 796811-Isopropylpiperidin-4-olHCID 5363146Diisopropyl azodicarboxylateHCID 13662999Methyl 5-hydroxybenzo[b]thiophene-2-carboxylate

Product 1

HCID 687252665-(1-Isopropyl-piperidin-4-yloxy)-benzo[b]thiophene-2-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The above prepared 5-hydroxy-benzo[b]thiophene-2-carboxylic acid methyl ester (0.143 g, 0.687 mmol) was dissolved in 3.4 mL of THF and treated successively at 10° C. with 1-isopropyl-piperidin-4-ol (0.197 g, 2 eq.), triphenylphosphine (0.360 g, 2 eq.) and DIAD (0.267 mL, 2 eq.), and the mixture then kept at ambient temperature for another 2 h. Pouring onto crashed ice, twofold extraction with AcOEt, washing with water, drying over sodium sulfate, and evaporation of the solvents, followed by flash chromatography (SiO2, NEt3/AcOEt=5/95), delivered 0.222 g of the title compound as light yellow oil.

Workup

  1. additionPouring
  2. extractionice, twofold extraction with AcOEt
  3. washwashing with water
  4. dry with materialdrying over sodium sulfate, and evaporation of the solvents

Sources & evidence

ORD record
ord-0e3bb16c37384e02ac45d446f93c3223
Source dataset
uspto-grants-2009_05
Patent number
US07534788B2

Reaction notes

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