Heptane → HCID 90203887, compound

HRID 1480231Notes

Reaction equation

HRID 1480231 reaction equation
C([N-]C(C)C)(C)C.[Li+].[CH3:9][C:10]1[N:11]=[CH:12][S:13][CH:14]=1.[CH3:15][C:16]([S:19]([N:21]=[C:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1)=[O:20])([CH3:18])[CH3:17].C[Al](C)C.CCCCCCC>C1COCC1.C1(C)C=CC=CC=1>[CH3:18][C:16]([S:19]([NH:21][C:22]1([C:12]2[S:13][CH:14]=[C:10]([CH3:9])[N:11]=2)[CH2:23][CH2:24][O:25][CH2:26][CH2:27]1)=[O:20])([CH3:15])[CH3:17]

Participants

8

Reactant 5

HCID 8900HeptaneHCID 127484-MethylthiazoleHCID 2724682Lithium diisopropylamideHCID 16682925TrimethylaluminumHCID 59599164HCID 59599164, compound

Product 1

HCID 90203887HCID 90203887, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

A 2.0M solution of lithium diisopropylamide in THF (492 μl, 984 μmol) was added dropwise to a solution of 4-methylthiazole (97.5 mg, 984 μmol) in dry THF (0.3 ml) cooled to −78° C. and once the addition was complete the reaction was stirred for 30 minutes at −78° C. followed by addition of dry toluene (0.6 ml). To a solution of 2-methyl-N-(2H-pyran-4(3H,5H,6H)-ylidene)propane-2-sulfinamide (CAN 861857-62-7, 100 mg, 492 μmol) in dry toluene (1 mL) was added a 2.0M solution of trimethylaluminum in heptane (271 μl, 541 μmol). The former solution was then added to the reaction mixture cooled at −78° C. The reaction was allowed to warm up to room temperature overnight. The reaction was quenched by the addition of a saturated aqueous solution of ammonium chloride and was then diluted with ethyl acetate. The bi-phasic mixture was poured into a separatory funnel and extracted. The organic phase was collected, dried over sodium sulfate and evaporated down to dryness. The crude material was purified by flash chromatography on silica eluting with a dichloromethane/methanol gradient to yield the title compound (102 mg, 69%). MS (ESI, m/z): 303.5 (M+H+).

Workup

  1. additiononce the addition
  2. additionThe former solution was then added to the reaction mixture
  3. temperaturecooled at −78° C
  4. temperatureto warm up to room temperature overnight
  5. customThe reaction was quenched by the addition of a saturated aqueous solution of ammonium chloride
  6. additionwas then diluted with ethyl acetate
  7. additionThe bi-phasic mixture was poured into a separatory funnel
  8. extractionextracted
  9. customThe organic phase was collected
  10. dry with materialdried over sodium sulfate
  11. customevaporated down to dryness
  12. customThe crude material was purified by flash chromatography on silica eluting with a dichloromethane/methanol gradient

Sources & evidence

ORD record
ord-372c2a2a3dd145c2a634773624fbfc3f
Source dataset
uspto-grants-2016_08
Patent number
US09409866B2

Reaction notes

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