Dichloromethane → (7R,7aR)-2-Chloro-4-(7-hydroxy-7a-methyl-1,3-dioxotetrahydropyrrolo[1,2-c]imidazol-2-yl)-3-methylbenzonitrile

HRID 501613ノート

反応式

HRID 501613 の反応式
[Si]([O:8][C@H:9]1[C@@:16]2([CH3:17])[N:12]([C:13](=[O:29])[N:14]([C:19]3[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[C:21]([Cl:27])[C:20]=3[CH3:28])[C:15]2=[O:18])[CH2:11][CH2:10]1)(C(C)(C)C)(C)C.C([O-])(O)=O.[Na+].C(Cl)Cl>C1COCC1>[Cl:27][C:21]1[C:20]([CH3:28])=[C:19]([N:14]2[C:15](=[O:18])[C@@:16]3([CH3:17])[C@H:9]([OH:8])[CH2:10][CH2:11][N:12]3[C:13]2=[O:29])[CH:26]=[CH:25][C:22]=1[C:23]#[N:24]

参加物

5

反応物 3

HCID 6344DichloromethaneHCID 516892Sodium BicarbonateHCID 59754338(7R,7aR)-4-[7-(tert-Butyldimethylsilanyloxy)-7a-methyl-1,3-dioxotetrahydropyrrolo[1,2-c]imidazol-2-yl]-2-chloro-3-methylbenzonitrile

生成物 1

HCID 59754283(7R,7aR)-2-Chloro-4-(7-hydroxy-7a-methyl-1,3-dioxotetrahydropyrrolo[1,2-c]imidazol-2-yl)-3-methylbenzonitrile収率 71.5%

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 (7R,7aR)-4-[7-(tert-Butyldimethylsilanyloxy)-7a-methyl-1,3-dioxotetrahydropyrrolo[1,2-c]imidazol-2-yl]-2-chloro-3-methylbenzonitrile (60B) (32 mg, 0.07 mmol) in THF (2 mL) in a plastic vial was cooled to 0° C. HF/pyridine complex (0.12 mL) was added and the reaction was stirred at 0° C. for 1 h and at rt overnight. Saturated aqueous NaHCO3 and CH2Cl2 were added. The layers were separated and the organic layer was concentrated under reduced pressure. The residue was purified via chromatography (silica gel) eluting with 75% EtOAc in hexane to provide the title compound (16 mg). LC/MS m/z 320 [M+H]+.

後処理

  1. additionHF/pyridine complex (0.12 mL) was added
  2. customThe layers were separated
  3. concentrationthe organic layer was concentrated under reduced pressure
  4. customThe residue was purified via chromatography (silica gel)
  5. washeluting with 75% EtOAc in hexane

出典と根拠

ORDレコード
ord-8c9da2874b74464abd5d9b667123e147
出典データセット
uspto-grants-2010_08
特許番号
US07772267B2

反応ノート

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