Cyclobutanone → HCID 68292090, compound

HRID 1504978Notes

Reaction equation

HRID 1504978 reaction equation
[Si]([C:5]#[N:6])(C)(C)C.[S:7]1[CH:11]=[CH:10][N:9]=[C:8]1[CH2:12][CH2:13][CH2:14][C:15]1[N:20]=[CH:19][C:18]([NH2:21])=[CH:17][CH:16]=1.[C:22]1(=O)[CH2:25][CH2:24][CH2:23]1>[Cl-].[Cl-].[Zn+2]>[S:7]1[CH:11]=[CH:10][N:9]=[C:8]1[CH2:12][CH2:13][CH2:14][C:15]1[N:20]=[CH:19][C:18]([NH:21][C:22]2([C:5]#[N:6])[CH2:25][CH2:24][CH2:23]2)=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 14496CyclobutanoneHCID 82115Trimethylsilyl cyanideHCID 68292813HCID 68292813, compound

Product 1

HCID 68292090HCID 68292090, compoundYield 94.3%

Reagents, catalysts & solvents 1

HCID 3007855ZincchlorideCatalyst

Procedure

TMSCN (0.13 mL, 0.96 mmol) was added to a mixture of compound 139 (70 mg, 0.32 mmol), cyclobutanone (0.15 mL, 1.92 mmol) and ZnCl2 (4 mg, 0.03 mmol) with stirring. The reaction mixture was stirred at room temperature for 5 h, and concentrated in vacuo. The residue was diluted with water, and extracted with DCM. The combined organic layers were washed with brine, dried over Na2SO4 and concentrated to dryness to give compound 141 (90 mg) as a light yellow oil. The crude product was used directly for the next step without purification.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 5 h
  2. concentrationconcentrated in vacuo
  3. additionThe residue was diluted with water
  4. extractionextracted with DCM
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-ee13d63bdb5e4735b661c79884b389f5
Source dataset
uspto-grants-2015_12
Patent number
US09216957B2

Reaction notes

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