Tetrabutylammonium Fluoride → 4-[(1S,7S,7aR)-7-Hydroxy-1-methyl-3-oxo-hexahydropyrrolo[1,2-c]imidazol-2-yl]-2-chloro-3-methylbenzonitrile

HRID 751136노트

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HRID 751136 반응식
[O:1]([C@@H:9]1[C@@H:16]2[N:12]([C:13](=[O:28])[N:14]([C:18]3[CH:25]=[CH:24][C:21]([C:22]#[N:23])=[C:20]([Cl:26])[C:19]=3[CH3:27])[C@H:15]2[CH3:17])[CH2:11][CH2:10]1)[Si](C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[OH:1][C@@H:9]1[C@@H:16]2[N:12]([C:13](=[O:28])[N:14]([C:18]3[CH:25]=[CH:24][C:21]([C:22]#[N:23])=[C:20]([Cl:26])[C:19]=3[CH3:27])[C@H:15]2[CH3:17])[CH2:11][CH2:10]1

참가 물질

4

반응물 2

HCID 2724141Tetrabutylammonium FluorideHCID 167337644-[(1S,7S,7aR)-7-tert-Butyldimethylsilanoxy-1-methyl-3-oxo-hexahydro-pyrrolo[1,2-c]imidazol-2-yl]-2-chloro-3-methylbenzonitrile

생성물 1

HCID 167337664-[(1S,7S,7aR)-7-Hydroxy-1-methyl-3-oxo-hexahydropyrrolo[1,2-c]imidazol-2-yl]-2-chloro-3-methylbenzonitrile수율 69.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 61J (369 mg) in THF (4 mL) was added TBAF (1.0 M in THF, 1.3 mL). The reaction was stirred at rt for 1 h. The reaction was extracted with EtOAc which was washed three times with water, dried over MgSO4, filtered and concentrated. Purification by reverse phase HPLC (Phenoenex Luna 20×100 mm S5 C18, 10 min. grad, 20 mL/min, 20-100% B solvent, A=10% MeOH/water+0.1% TFA, B=90% MeOH/Water+0.1% TFA) provided the title compound (186 mg): MS (ES) m/z 306.42 [M+H]+

후처리

  1. extractionThe reaction was extracted with EtOAc which
  2. washwas washed three times with water
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by reverse phase HPLC (Phenoenex Luna 20×100 mm S5 C18, 10 min.

출처 및 근거

ORD 기록
ord-06cdf34cb8b04f9e8b97fd26a0f9e9c8
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07405234B2

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