Sodium Cyanide → HCID 21309641, compound

HRID 1416648Notes

Reaction equation

HRID 1416648 reaction equation
[CH3:1][N:2]1[C:6](=O)[C@H:5](OS(C)(=O)=O)[CH2:4][C@H:3]1[CH2:13][O:14][C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1.[C-:21]#[N:22].[Na+]>CN(C=O)C.O>[C:21]([C@@H:5]1[CH2:6][N:2]([CH3:1])[C@H:3]([CH2:13][O:14][C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)[CH2:4]1)#[N:22]

Participants

5

Reactant 2

HCID 8929Sodium CyanideHCID 21309697HCID 21309697, compound

Product 1

HCID 21309641HCID 21309641, compoundYield 35.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 300 mg (1.05 mmol) of 3-((trans-1-methyl-4-methanesulfonyloxy-5-oxo-2(S)-pyrrolidinyl)-methoxy)pyridine, prepared as in Example 88a above, dissolved in 7 mL of 6:1 DMF:H2O was added 0.51 g (10.5 mmol) of NaCN, and the reaction mixture was heated at 100° C. for 5 hours. The reaction mixture was cooled, diluted with water, and extracted with chloroform. The extract was dried over MgSO4 and concentrated. The residue was purified on a silica gel column, eluting with 100:2 chloroform:methanol, to give 80 mg of the title compound.

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with chloroform
  3. dry with materialThe extract was dried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was purified on a silica gel column
  6. washeluting with 100:2 chloroform

Sources & evidence

ORD record
ord-c23caf71d58f45d0ab2f470d23c23549
Source dataset
uspto-grants-1999_06
Patent number
US05914328

Reaction notes

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