Acetic Acid → HCID 10967752, compound

HRID 1873117Notes

Reaction equation

HRID 1873117 reaction equation
[CH3:1][S:2][C:3]1[CH:18]=[CH:17][C:6]2[C@:7]3([CH3:16])[C@@H:12]([CH2:13][CH2:14][C:5]=2[CH:4]=1)[NH:11][C:10](=[O:15])[CH2:9][CH2:8]3.[CH3:19]C(C)([O-])C.[K+].CI.C(O)(=O)C>O1CCCC1.CN(C)C=O>[CH3:19][N:11]1[C@H:12]2[C@@:7]([CH3:16])([C:6]3[CH:17]=[CH:18][C:3]([S:2][CH3:1])=[CH:4][C:5]=3[CH2:14][CH2:13]2)[CH2:8][CH2:9][C:10]1=[O:15]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 6328Methyl iodideHCID 10199120HCID 10199120, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 10967752HCID 10967752, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

(+)-(4aR)-(10bR)-8-methylthio-10b-methyl-1,2,3,4,4a,5,6,10b-octahydrobenzo[f]quinolin-3-one (0.423 grams, 1.62 mmol, 1.0 equivalents) was treated with potassium t-butoxide (1.86 mL as a 1.0 M solution in tetrahydrofuran, 1.15 equivalents) in dimethylformamide (1.6 mL) at approximately 0° C. After stirring 5 minutes, methyl iodide (0.116 mL, 1.15 equivalents) was added and the mixture allowed to stir for 2 hours at 0° C. The mixture was then treated with approximately 100 mg of acetic acid and solvents were removed in a stream of nitrogen. The solid was dissolved in approximately 50 mL of methylene chloride and washed twice with water. The extracts were dried (4 molecular sieves) and filtered over silica gel (2 grams, washed with ethyl acetate containing 2% methanol). The solid from the evaporation of the methylene chloride extracts was chromatographed on silica gel with methylene chloride, ethyl acetate and methanol (50:50:1) as the eluent. (GC).

Workup

  1. stirringto stir for 2 hours at 0° C
  2. customwere removed in a stream of nitrogen
  3. dissolutionThe solid was dissolved in approximately 50 mL of methylene chloride
  4. washwashed twice with water
  5. customThe extracts were dried (4 molecular sieves)
  6. filtrationfiltered over silica gel (2 grams, washed with ethyl acetate containing 2% methanol)
  7. customThe solid from the evaporation of the methylene chloride extracts
  8. customwas chromatographed on silica gel with methylene chloride, ethyl acetate and methanol (50:50:1) as the eluent

Sources & evidence

ORD record
ord-48ced80b16e74b6d87d1005982bb2954
Source dataset
uspto-grants-2000_08
Patent number
US06111110

Reaction notes

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