Potassium Carbonate → HCID 59837354, compound

HRID 272990Notes

Reaction equation

HRID 272990 reaction equation
S([CH2:11][N+:12]#[C-:13])(C1C=CC(C)=CC=1)(=O)=O.[N:14]1([CH2:19][CH2:20][CH2:21][O:22][C:23]2[CH:28]=[CH:27][C:26]([C:29]3([CH:35]=[O:36])[CH2:34][CH2:33][O:32][CH2:31][CH2:30]3)=[CH:25][CH:24]=2)[CH2:18][CH2:17][CH2:16][CH2:15]1.C(=O)([O-])[O-].[K+].[K+]>CO>[N:14]1([CH2:19][CH2:20][CH2:21][O:22][C:23]2[CH:28]=[CH:27][C:26]([C:29]3([C:35]4[O:36][CH:13]=[N:12][CH:11]=4)[CH2:30][CH2:31][O:32][CH2:33][CH2:34]3)=[CH:25][CH:24]=2)[CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 161915Tosylmethyl isocyanideHCID 598374274-[4-(3-pyrrolidin-1-ylpropoxy)phenyl]tetrahydro-2H-pyran-4-carbaldehyde

Product 1

HCID 59837354HCID 59837354, compoundYield 2.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Tosylmethyl isocyanide (370 mg, 1.89 mmol) was added to a solution of 4-[4-(3-pyrrolidin-1-ylpropoxy)phenyl]tetrahydro-2H-pyran-4-carbaldehyde (500 mg, 1.58 mmol) and potassium carbonate (652 mg, 4.73 mmol) in methanol (7 ml). The reaction mixture was heated at reflux for 3 hours. The reaction mixture was partitioned between ethyl acetate (2×75 ml) and water (20 ml). The organic layers were combined, dried over sodium sulphate, filtered and concentrated in vacuo. The crude product was taken up in 2N hydrochloric acid (3 ml) and stirred at room temperature for 1.5 hours. The mixture was then partitioned between aqueous sodium carbonate and dichloromethane (2×75 ml). The combined organic layers were dried over sodium sulphate, filtered and concentrated in vacuo. The crude product was purified by flash chromatography on silica gel eluting with dichloromethane:methanol:ammonia (95:5:0.5 by volume) to provide the title compound (12 mg, 2%). 1H NMR (400 MHz, CD3OD) δ 1.81-1.85 (m, 4H), 1.97-2.02 (m, 2H), 2.25-2.31 (m, 2H), 2.38-2.43 (m, 2H), 2.60-2.63 (m, 4H), 2.69 (t, 2H), 3.61 (t, 2H), 3.78-3.83 (m, 2H), 4.01 (t, 2H), 6.87 (d, 2H), 6.98 (s, 1H), 7.22 (d, 2H), 8.09 (s, 1H). LRMS APCI+ m/z 357 [MH]+.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 3 hours
  3. customThe reaction mixture was partitioned between ethyl acetate (2×75 ml) and water (20 ml)
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe mixture was then partitioned between aqueous sodium carbonate and dichloromethane (2×75 ml)
  8. dry with materialThe combined organic layers were dried over sodium sulphate
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customThe crude product was purified by flash chromatography on silica gel eluting with dichloromethane:methanol:ammonia (95:5:0.5 by volume)

Sources & evidence

ORD record
ord-15f15641d7d049ab990bc45ca2e71001
Source dataset
uspto-grants-2008_11
Patent number
US07456164B2

Reaction notes

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