Acetone → HCID 178431381, compound

HRID 46135Notes

Reaction equation

HRID 46135 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-4b0a637ae3074fdab316f792c7678574
Source dataset
uspto-grants-2013_09
Patent number
US08541592B2

Reaction notes

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