Thiazole → HCID 59298225, compound

HRID 557894Notes

Reaction equation

HRID 557894 reaction equation
C([Li])CCC.[S:6]1[CH:10]=[CH:9][N:8]=[CH:7]1.[O:11]=[C:12]1[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13]1>CCCCCC.C1COCC1>[OH:11][C:12]1([C:7]2[S:6][CH:10]=[CH:9][N:8]=2)[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13]1

Participants

6

Reactant 3

HCID 9256ThiazoleHCID 471360Tert-butyl 3-oxopyrrolidine-1-carboxylateHCID 178418339Butyllithium

Product 1

HCID 59298225HCID 59298225, compoundYield 70.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

1.600 M of n-Butyllithium in hexane (1.0×10−1 mL) was added to 1,3-thiazole (0.958 mL, 0.0135 mol) in THF (20 mL) at −78° C. After 30 minutes, tert-butyl 3-oxopyrrolidine-1-carboxylate (2.50 g, 0.0135 mol) in THF (10 mL) was added, and the mixture was slowly warmed to room temperature overnight. The reaction was quenched with water, and the reaction mixture was extracted with ethyl acetate, dried with MgSO4, filtered and concentrated. The residue was purified by flash column (50% EtOAc/hexanes to pure EtOAc) to give the desired product (2.57 g, 70%).

Workup

  1. customThe reaction was quenched with water
  2. extractionthe reaction mixture was extracted with ethyl acetate
  3. dry with materialdried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash column (50% EtOAc/hexanes to pure EtOAc)

Sources & evidence

ORD record
ord-7dbf28b5dad3481eac69594b652fb1bd
Source dataset
uspto-grants-2011_11
Patent number
US08058288B2

Reaction notes

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