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

HRID 1696981

反応式

HRID 1696981 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 9811564Bis(dibenzylideneacetone)palladium触媒

実験手順

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. Triethylamine (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, dichloromethane/methanol 25:1). 1H nmr (CDCl3, 400 MHz); 8.30(s, 1H), 6.40(m, 1H), 5.90(m, 1H), 5.50(m, 1H), 4.95(m, 1H), 3.05(m, 1H), 2.10(m, 1H), MS (ES+) m/e 271 (MH+).

後処理

  1. customare placed in an oven-dried flask under an atmosphere of argon
  2. customDry
  3. customdeoxygenated THF (80 ml)
  4. additionis added
  5. additionTriethylamine (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

出典と根拠

ORDレコード
ord-2c6675117449426694dacfbfbd9faf86
出典データセット
uspto-grants-2012_04
特許番号
US08163754B2

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