Borane;tetrahydrofuran → HCID 11994549、化合物

HRID 395280ノート

反応式

HRID 395280 の反応式
[O:1]=[C:2]1[N:10]([CH2:11][CH2:12][CH3:13])[C:9]2[N:8]=[C:7]([C:14]34[CH2:21][CH2:20][C:17]([C:22](O)=[O:23])([CH2:18][CH2:19]3)[CH2:16][CH2:15]4)[NH:6][C:5]=2[C:4](=[O:25])[NH:3]1.B.C1COCC1>C1COCC1>[OH:23][CH2:22][C:17]12[CH2:18][CH2:19][C:14]([C:7]3[NH:6][C:5]4[C:4](=[O:25])[NH:3][C:2](=[O:1])[N:10]([CH2:11][CH2:12][CH3:13])[C:9]=4[N:8]=3)([CH2:21][CH2:20]1)[CH2:15][CH2:16]2

参加物

4

反応物 2

HCID 2723981Borane;tetrahydrofuranHCID 22219469HCID 22219469、化合物

生成物 1

HCID 11994549HCID 11994549、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

4-(2,6-Dioxo-3-propyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-bicyclo[2.2.2]octane-1-carboxylic acid (3.2 g, 9.25 mmol) was dissolved in 100 mL of anhydrous THF and cooled to 0° C. Borane-THF (1.0 M in THF, 18.5 mL, 2 eq) was added and the reaction mixture was stirred at 0° C. for 10 min, then warmed to rt and stirred for 48 h. The reaction mixture was then carefully quenched with 10 mL of MeOH and then concentrated under reduced pressure. The resulting residue was dissolved in 20 mL of MeOH and concentrated under reduced pressure. This treatment was repeated four more times to afford the desired alcohol.

後処理

  1. temperaturewarmed to rt
  2. stirringstirred for 48 h
  3. customThe reaction mixture was then carefully quenched with 10 mL of MeOH
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe resulting residue was dissolved in 20 mL of MeOH
  6. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-40f295149812466f8490dae37a200f7a
出典データセット
uspto-grants-2003_08
特許番号
US06605601B2

反応ノート

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