Potassium Cyanide → HCID 22458268, compound

HRID 2185568Notes

Reaction equation

HRID 2185568 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:24])[CH2:9][CH2:10][CH:11]2[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]2)=[CH:4][CH:3]=1.[Li+].[I-].[C-:27]#[N:28].[K+].C([O-])([O-])=O.[K+].[K+].C(OC(OC(C)(C)C)=O)(OC(C)(C)C)=O>CS(C)=O.CCOC(C)=O>[C:27]([C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:24])[CH2:9][CH2:10][CH:11]2[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]2)=[CH:4][CH:3]=1)#[N:28]

Participants

8

Reactant 5

HCID 9032Potassium CyanideHCID 11430Potassium CarbonateHCID 66321Lithium iodideHCID 90495Di-tert-butyl dicarbonateHCID 22458227HCID 22458227, compound

Product 1

HCID 22458268HCID 22458268, compoundYield 12%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
135 °C

Procedure

A round bottom flask was charged with 4-(3-(4-fluoro-phenyl)-3-oxopropyl)-1-tert-butoxycarbonyl-piperidine (614 mg, 1.83 mmol, from Step C), LiI, (294 mg, 2.2 mmol), KCN (358 mg, 5.5 mmol), and K2CO3 (3 grams, 22 mmol) in 30 mL DMSO. The mixture was heated to 135° C. for 72 h. The solution was cooled to room temperature and di-tert-butyl dicarbonate (500 mg, 2.3 mmol) was added. After 1 h the mixture was diluted with 100 mL EtOAc and the organic phase washed with water (50 mL) and sat'd NaCl (2×50 mL), then dried over Na2SO4 and concentrated. Flash chromatography (3/1 hexane/EtOAc eluant) afforded 75 mg (12%) of the title compound.

Workup

  1. temperatureThe solution was cooled to room temperature
  2. washthe organic phase washed with water (50 mL) and sat'd NaCl (2×50 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-8c74b62cf5d9418b96edc19b4c0bdd51
Source dataset
uspto-grants-2002_06
Patent number
US06399619B1

Reaction notes

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