Sodium Sulfite → tert-Butyl (2S)-2-(5-bromo-1H-imidazol-2-yl)pyrrolidine-1-carboxylate

HRID 2364845노트

반응식

HRID 2364845 반응식
[Br:1][C:2]1[N:3]=[C:4]([C@@H:8]2[CH2:12][CH2:11][CH2:10][N:9]2[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[NH:5][C:6]=1Br.[O-]S([O-])=O.[Na+].[Na+]>O1CCOCC1.O>[Br:1][C:2]1[NH:3][C:4]([C@@H:8]2[CH2:12][CH2:11][CH2:10][N:9]2[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[N:5][CH:6]=1

참가 물질

5

반응물 2

HCID 24437Sodium SulfiteHCID 56605191(S)-tert-Butyl 2-(4,5-dibromo-1H-imidazol-2-yl)pyrrolidine-1-carboxylate

생성물 1

HCID 56605192tert-Butyl (2S)-2-(5-bromo-1H-imidazol-2-yl)pyrrolidine-1-carboxylate수율 52.2%

시약·촉매·용매 2

HCID 962Water용매2회HCID 312751,4-Dioxane용매

실험 절차

A mixture of Example 126D (12.5 g, 31.5 mmol) in dioxane (400 mL) and H2O (400 mL) had a solution of Na2SO3 (43.7 g, 347 mmol) in H2O (400 mL) added and was heated to reflux for 21 hours. The mixture was concentrated to half volume and extracted with CH2Cl2 (3×200 mL). The organic was then washed with brine, dried (MgSO4), filtered and concentrated. Purification by trituration (CH2Cl2, tBuOMe, and Hexanes) afforded 5.2 g (52%) of the title compound. MS (ESI) m/z 317 (M+H)+.

후처리

  1. additionadded
  2. temperaturewas heated
  3. temperatureto reflux for 21 hours
  4. concentrationThe mixture was concentrated to half volume
  5. extractionextracted with CH2Cl2 (3×200 mL)
  6. washThe organic was then washed with brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customPurification by trituration (CH2Cl2, tBuOMe, and Hexanes)

출처 및 근거

ORD 기록
ord-e90ccd43260c40d491d1625593c4786f
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08691938B2

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