Sodium Cyanide → HCID 21309641, compound

HRID 617358Notes

Reaction equation

HRID 617358 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, compound2×

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 Exanmple 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-5e43ff58401e4f14b3491fcdbf160c37
Source dataset
uspto-grants-1999_09
Patent number
US05948793

Reaction notes

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