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

HRID 493179노트

반응식

HRID 493179 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-0e3bb16c37384e02ac45d446f93c3223
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07534788B2

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