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

HRID 501613노트

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HRID 501613 반응식
[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]

참가 물질

5

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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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

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]+.

후처리

  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

출처 및 근거

ORD 기록
ord-8c9da2874b74464abd5d9b667123e147
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07772267B2

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