Iodine → HCID 68721370, compound

HRID 885113Notes

Reaction equation

HRID 885113 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.C([Li])CCC.[C:11]([N:18]1[CH2:22][CH2:21][C:20](=[O:23])[CH2:19]1)([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12].C([N-]C(C)C)(C)C.[Li+].[I:32]I>O1CCCC1>[OH:23][C:20]1([C:2]2[S:1][C:5]([I:32])=[CH:4][N:3]=2)[CH2:21][CH2:22][N:18]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:19]1

Participants

7

Reactant 5

HCID 807IodineHCID 9256ThiazoleHCID 471360Tert-butyl 3-oxopyrrolidine-1-carboxylateHCID 2724682Lithium diisopropylamideHCID 178418339Butyllithium

Product 1

HCID 68721370HCID 68721370, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a cold (−78° C.) solution of thiazole (0.382 mL, 5.41 mmol) in tetrahydrofuran (30 mL) was added n-butyllithium (3.38 mL, 5.41 mmol, 1.6 M in hexane) dropwise. After 15 minutes, N-boc-3-pyrrolidinone (0.49 mL, 5.41 mmol) was added in a single portion. After 30 minutes, lithium diisopropylamide (5.41 mL, 5.41 mmol, 1.0 M in tetrahydrofuran) was added dropwise. The reaction was allowed to stir for an additional 30 minutes, after which a solution of I2 (1.37 g, 5.4 mmol) in tetrahydrofuran (10 mL) was added dropwise. After 10 minutes, the reaction was then quenched by the addition of saturated aqueous Na2S2O3 (100 mL) and ethyl acetate (100 mL) and allowed to warm to ambient temperature. The layers were separated, and the aqueous was extracted with additional ethyl acetate (2×100 mL). The combined organics were dried with anhydrous Na2SO4 filtered, and concentrated to give a dark solid. The residue was purified by chromatography on SiO2 gel, eluting with 50% ethyl acetate in hexanes, to give the title product as a solid. MS (ESI) m/z 397 [M+H]+.

Workup

  1. waitAfter 30 minutes
  2. waitAfter 10 minutes
  3. customthe reaction was then quenched by the addition of saturated aqueous Na2S2O3 (100 mL) and ethyl acetate (100 mL)
  4. customThe layers were separated
  5. extractionthe aqueous was extracted with additional ethyl acetate (2×100 mL)
  6. dry with materialThe combined organics were dried with anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give a dark solid
  10. customThe residue was purified by chromatography on SiO2 gel
  11. washeluting with 50% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-d353633fc4a74e1ba8c295a8c15440d5
Source dataset
uspto-grants-2012_08
Patent number
US08242139B2

Reaction notes

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