Methyl iodide → HCID 54180864, compound

HRID 1780434Notes

Reaction equation

HRID 1780434 reaction equation
[CH3:1]C(C)([O-])C.[K+].C(O)(C)(C)C.[CH3:12][C@@:13]12[C:22]3[CH:23]=[CH:24][C:25]([S:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)=[CH:26][C:21]=3[CH2:20][CH2:19][C@H:18]1[NH:17][C:16](=[O:34])[CH2:15][CH2:14]2.CI>C(OCC)(=O)C>[CH3:1][N:17]1[C@H:18]2[C@@:13]([CH3:12])([C:22]3[CH:23]=[CH:24][C:25]([S:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)=[CH:26][C:21]=3[CH2:20][CH2:19]2)[CH2:14][CH2:15][C:16]1=[O:34]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 6386tert-ButanolHCID 23665647Potassium tert-butoxideHCID 54218849HCID 54218849, compound

Product 1

HCID 54180864HCID 54180864, compoundYield 471.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Potassium t-butoxide (0.22 g, 1.9 mmol) was added to 5 mL of t-butanol in a 25 mL round bottom flask. The (4aR)-(10bR)-10b-methyl-8-phenylthio-1,2,3,4,4a,5,6,10b-octahydrobenzo[f]-quinolin-3-one, (0.183 g, 0.566 mmol) was added followed by methyl iodide while cooling briefly in an ice bath. The mixture was allowed to stir at room temperature for 18 h before diluting with ethyl acetate and filtering to remove inorganics. Filtrate was concentrated in vacuo to give a oil which was triturated in hexane/diethyl ether to facilitate crystallization. Recrystallization from ethyl acetate/hexane gave 0.90 g of white crystals: mp 109°-112°; FD MS 337 M+; Calcd for C21H23N1O1S1.

Workup

  1. temperaturewhile cooling briefly in an ice bath
  2. filtrationfiltering
  3. customto remove inorganics
  4. concentrationFiltrate was concentrated in vacuo
  5. customto give a oil which
  6. customwas triturated in hexane/diethyl ether
  7. customcrystallization
  8. customRecrystallization from ethyl acetate/hexane

Sources & evidence

ORD record
ord-d05ef3cd609e4579b10f561b27efd0be
Source dataset
uspto-grants-1997_05
Patent number
US05629007

Reaction notes

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