Acetone → HCID 178431381, compound

HRID 852801Notes

Reaction equation

HRID 852801 reaction equation
[C@@H:1]12[CH2:7][C@@H:4]([CH2:5][CH2:6]1)[CH2:3][C@@H:2]2[NH:8][C:9]1[S:10][CH:11]([CH2:15][CH2:16]Br)[C:12](=[O:14])[N:13]=1.[Li+].[CH3:19]C([N-]C(C)C)C.[CH3:26][C:27](C)=[O:28]>C1COCC1>[C@@H:1]12[CH2:7][C@@H:4]([CH2:5][CH2:6]1)[CH2:3][C@@H:2]2[NH:8][C:9]1[S:10][C:11]2([CH2:26][CH2:27][O:28][C:15]2([CH3:16])[CH3:19])[C:12](=[O:14])[N:13]=1

Participants

5

Reactant 3

HCID 180AcetoneHCID 2724682Lithium diisopropylamideHCID 178518178HCID 178518178, compound

Product 1

HCID 178431381HCID 178431381, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 2-((1S,2S,4R)-bicyclo[2.2.1]heptan-2-ylamino)-5-(2-bromoethyl)thiazol-4(5H)-one (134 mg, 0.5 mmol) in THF (1 mL) at −78° C. was added LDA (2.0 N, 1.25 ml). After 5 min, acetone (500 uL) was added, and the reaction mixture was stirred for 3 h at −78° C. The resulting reaction mixture was poured into a sat'd NaH2PO4 and extracted with EtOAc. The organic layer was dried over MgSO4, filtered and concentrated in vacuo. The crude residue was purified through flash chromatography (4:1; Hexane:EtOAc) to give 2-((1S,2S,4R)-bicyclo[2.2.1]hept-2-ylamino)-6,6-dimethyl-7-oxa-1-thia-3-azaspiro[4.4]non-2-en-4-one as a white solid. (MS (ES+): 295 (M+H)+), and 5-((1S,2S,4R)-bicyclo[2.2.1]hept-2-ylamino)-4-thia-6-azaspiro[2.4]hept-5-en-7-one as a white solid. MS (ES+): 237 (M+H)+.

Workup

  1. customThe resulting reaction mixture
  2. extractionextracted with EtOAc
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude residue was purified through flash chromatography (4:1; Hexane:EtOAc)

Sources & evidence

ORD record
ord-5ac6029bba5647ecbb0cdf35d71902ed
Source dataset
uspto-grants-2007_08
Patent number
US07253196B2

Reaction notes

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