N,N,N',N'-Tetramethylethylenediamine → HCID 86667345、化合物

HRID 334125

反応式

HRID 334125 の反応式
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH2:11][CH2:12][C:13]2([OH:16])[CH2:15][CH2:14]2)=[C:4]([N:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)[N:3]=1.CN(C)CCN(C)C.C([Li])CCC.CCCCCC.ClCC[I:45]>C1COCC1>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[C:7]([I:45])[N:8]2[CH2:11][CH2:12][C:13]2([OH:16])[CH2:15][CH2:14]2)=[C:4]([N:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)[N:3]=1

参加物

7

反応物 5

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 8058HexaneHCID 1364381-Chloro-2-iodoethaneHCID 86667343HCID 86667343、化合物HCID 178418339Butyllithium

生成物 1

HCID 86667345HCID 86667345、化合物収率 71.9%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

A solution of 1-(2-(2-chloro-6-morpholino-9H-purin-9-yl)ethyl)cyclopropanol (220 mg, 0.68 mmol) and N,N,N′,N′-tetramethylethylene-diamine (0.15 mL, 1.0 mmol) in THF (4.9 mL) was cooled to −42° C. and treated with a solution of 2.5M n-butyllithium in hexane (1.5 mL, 3.7 mmol) dropwise over 5 minutes. After 30 minutes at −42° C., 1-chloro-2-iodoethane (0.31 mL, 3.3 mmol) was added and the reaction mixture was slowly warmed to 0° C. over 1 hr. The mixture was quenched with a saturated solution of NH4Cl, and diluted with ethyl acetate. The aqueous layer was extracted into ethyl acetate (3×), and the combined organics were dried over sodium sulfate, filtered, and absorbed onto celite for purification by flash chromatography to afford 1-(2-(2-chloro-8-iodo-6-morpholino-9H-purin-9-yl)ethyl)cyclopropanol as a colorless oil (220 mg, 71%). LC/MS (ESI+): m/z 450 (M+H)

後処理

  1. customThe mixture was quenched with a saturated solution of NH4Cl
  2. additiondiluted with ethyl acetate
  3. extractionThe aqueous layer was extracted into ethyl acetate (3×)
  4. dry with materialthe combined organics were dried over sodium sulfate
  5. filtrationfiltered
  6. customabsorbed onto celite for purification by flash chromatography

出典と根拠

ORDレコード
ord-87381f2609c54f44a742010e8c1e2bdf
出典データセット
uspto-grants-2014_11
特許番号
US08883799B2

関連ノート

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