Triphenylphosphine → (1S,4R)-4-(2,6-Dichloro-9H-purin-9-yl)cyclopent-2-en-1-ol

HRID 215840

반응식

HRID 215840 반응식
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([NH:6][CH:7]=[N:8]2)=[C:4]([Cl:11])[N:3]=1.CC([O:15][C@H:16]1[CH:20]=[CH:19][C@@H:18](O)[CH2:17]1)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C@@H:19]2[CH2:20][C@H:16]([OH:15])[CH:17]=[CH:18]2)=[C:4]([Cl:11])[N:3]=1

참가 물질

5

반응물 3

HCID 11776TriphenylphosphineHCID 53244122,6-DichloropurineHCID 10154103rac-(1R,4S)-4-hydroxycyclopent-2-en-1-yl acetate

생성물 1

HCID 10378467(1S,4R)-4-(2,6-Dichloro-9H-purin-9-yl)cyclopent-2-en-1-ol

시약·촉매·용매 1

HCID 9811564Bis(dibenzylideneacetone)palladium촉매

실험 절차

2,6-Dichloropurine (10 g, 52.90 mmol), (1S,4R)-cis 4-acetoxy-2-cyclopenten-1-ol (10 g, 70.40 mmol), tris(dibenzylideneacetone)dipalladium(0) (3.20 g, 3.50 mmol) and polymer supported triphenylphosphine (3 mmol/g, 11.60 g, 35.00 mmol) are placed in an oven-dried flask under an atmosphere of argon. Dry deoxygenated THF (80 mL) is added and the reaction mixture is stirred gently for 5 minutes. TEA (20 mL) is added and the reaction mixture is stirred at 50° C. The reaction is shown to be complete by LCMS after 1 hour. The reaction mixture is allowed to cool, filtered and the solvent is removed in vacuo. The title compound is obtained after purification by flash column chromatography (silica, DCM:MeOH 25:1).

후처리

  1. customare placed in an oven-dried flask under an atmosphere of argon
  2. customDry
  3. customdeoxygenated THF (80 mL)
  4. additionis added
  5. additionTEA (20 mL) is added
  6. stirringthe reaction mixture is stirred at 50° C
  7. waitto be complete by LCMS after 1 hour
  8. temperatureto cool
  9. filtrationfiltered
  10. customthe solvent is removed in vacuo

출처 및 근거

ORD 기록
ord-4f16a5b7b5164838bfb0298f2cd8ca8a
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08193164B2

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