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

HRID 2364845ノート

反応式

HRID 2364845 の反応式
[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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 312751,4-Dioxane溶媒

実験手順

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)+.

後処理

  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)

出典と根拠

ORDレコード
ord-e90ccd43260c40d491d1625593c4786f
出典データセット
uspto-grants-2014_04
特許番号
US08691938B2

反応ノート

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