Cyclobutanone → HCID 68292161, compound

HRID 1504953Notes

Reaction equation

HRID 1504953 reaction equation
[Si]([C:5]#[N:6])(C)(C)C.[NH2:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][CH2:16][C:17]([NH:19][CH3:20])=[O:18])=[CH:10][CH:9]=1.[C:21]1(=O)[CH2:24][CH2:23][CH2:22]1>>[C:5]([C:21]1([NH:7][C:8]2[CH:9]=[CH:10][C:11]([CH2:14][CH2:15][CH2:16][C:17]([NH:19][CH3:20])=[O:18])=[CH:12][CH:13]=2)[CH2:24][CH2:23][CH2:22]1)#[N:6]

Participants

4

Reactant 3

HCID 14496CyclobutanoneHCID 82115Trimethylsilyl cyanideHCID 68292716HCID 68292716, compound

Product 1

HCID 68292161HCID 68292161, compoundYield 67%

Procedure

TMSCN (0.09 mL, 0.70 mmol) was added to a mixture of the compound 30 (90 mg, 0.47 mmol), cyclobutanone (0.05 mL, 0.70 mmol) and 12 (6 mg, 0.05 mmol) with stirring. The reaction mixture was stirred at room temperature for 10 min, and concentrated in vacuo. The residue was diluted with aq Na2SO3, and extracted with DCM. The combined organic layers were washed with aq Na2SO3 and brine, dried over Na2SO4 and concentrated. The residue was purified with silica gel column chromatography using Petroleum ether:Ethyl acetate (10:1) affording to compound 39 (85 mg, 67%) as a light yellow oil. 1H NMR (400 MHz, CDCl3) δ6.98 (d, 2H, J=8.4 Hz), 6.56 (d, 2H, J=8.4 Hz), 5.39 (br s, 1H), 2.66-2.76 (m, 5H), 2.50 (t, 2H, J=8.4 Hz), 2.28-2.40 (m, 2H), 2.10-2.22 (m, 2H), 2.08 (t, 2H, J=8.4 Hz), 1.80-1.90 (m, 2H).

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 10 min
  2. concentrationconcentrated in vacuo
  3. additionThe residue was diluted with aq Na2SO3
  4. extractionextracted with DCM
  5. washThe combined organic layers were washed with aq Na2SO3 and brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. customThe residue was purified with silica gel column chromatography

Sources & evidence

ORD record
ord-bdc62dbe98574f869e92a8fc3aa3e01b
Source dataset
uspto-grants-2015_12
Patent number
US09216957B2

Reaction notes

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