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

HRID 2364845Notes

Reaction equation

HRID 2364845 reaction equation
[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

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

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)+.

Workup

  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)

Sources & evidence

ORD record
ord-e90ccd43260c40d491d1625593c4786f
Source dataset
uspto-grants-2014_04
Patent number
US08691938B2

Reaction notes

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