Acetone → HCID 178431381, compound

HRID 2360297Notes

Reaction equation

HRID 2360297 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-ef3debec6b9d4b46bc4a050de9705e7c
Source dataset
uspto-grants-2014_04
Patent number
US08686011B2

Reaction notes

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