Sodium Cyanide → HCID 68681909, compound

HRID 2267102Notes

Reaction equation

HRID 2267102 reaction equation
FC(F)(F)S(O[C:7]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:10]2([CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]2)[CH2:9][CH:8]=1)(=O)=O.[C-:31]#[N:32].[Na+]>C(#N)C.[Cu]I.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:31]([C:7]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:10]2([CH2:11][CH2:12][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:14][CH2:15]2)[CH2:9][CH:8]=1)#[N:32]

Participants

6

Reactant 2

HCID 8929Sodium CyanideHCID 59600639HCID 59600639, compound

Product 1

HCID 68681909HCID 68681909, compoundYield 92.5%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 6342AcetonitrileSolvent

Procedure

A mixture of the triflate (A2) (447 mg, 1 mmol), sodium cyanide (100 mg, 2 mmol), copper (I) iodide (19 mg, 0.1 mmol) and tetrakis(triphenylphosphine)palladium(0) (58 mg, 0.05 mmol) in acetonitrile (10 ml) was degassed and heated under reflux under nitrogen for 4 h. After concentration, the residue was directly purified by flash chromatography (hexane/EtOAc 8:2) to give tert-butyl 4-cyano-2H-spiro[naphthalene-1,4′-piperidine]-1′-carboxylate (A3) (300 mg). LC-MS: m/e=269.0 (M+H−C(CH3)3. Rt=3.75 min. 1H-NMR (500 MHz, DMSO-d6): 7.49 (d, 1H), 7.42-7.36 (m, 3H), 7.09 (t, 1H), 3.81 (br. d, 2 H), 3.03 (br. s, 2H), 2.67 (d, 2H), 1.70 (td, 2H), 1.62 (d, 2H), 1.41 (s, 9H),

Workup

  1. customwas degassed
  2. temperatureheated
  3. temperatureunder reflux under nitrogen for 4 h
  4. concentrationAfter concentration
  5. customthe residue was directly purified by flash chromatography (hexane/EtOAc 8:2)

Sources & evidence

ORD record
ord-0eeda241809d4d33838702d5b2b5eb74
Source dataset
uspto-grants-2010_12
Patent number
US07858790B2

Reaction notes

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