Sodium Cyanide → HCID 68575543, compound

HRID 273083Notes

Reaction equation

HRID 273083 reaction equation
[N:1]1([CH2:6][CH2:7][CH2:8][O:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3([CH:22]=[O:23])[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)=[CH:12][CH:11]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:24][C:25]1[CH:30]=[CH:29][C:28]([S:31]([CH2:34][N+:35]#[C-:36])(=[O:33])=[O:32])=[CH:27][CH:26]=1.[C-]#N.[Na+]>CCO>[N:1]1([CH2:6][CH2:7][CH2:8][O:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3([CH:22]4[O:23][CH:36]=[N:35][CH:34]4[S:31]([C:28]4[CH:29]=[CH:30][C:25]([CH3:24])=[CH:26][CH:27]=4)(=[O:33])=[O:32])[CH2:17][CH2:18][O:19][CH2:20][CH2:21]3)=[CH:12][CH:11]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 8929Sodium CyanideHCID 161915Tosylmethyl isocyanideHCID 598374274-[4-(3-pyrrolidin-1-ylpropoxy)phenyl]tetrahydro-2H-pyran-4-carbaldehyde

Product 1

HCID 68575543HCID 68575543, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-[4-(3-pyrrolidin-1-ylpropoxy)phenyl]tetrahydro-2H-pyran-4-carbaldehyde (500 mg, 1.6 mmol) and TosMIC (340 mg, 1.7 mmol) were dissolved in EtOH (20 ml), to which NaCN (12 mg, 0.25 mmol) was added. The solution immediately turned pale yellow and was allowed to stir for 2 hours at room temperature. The solvent was removed in vacuo and the residue was taken up in DCM (10 ml) and washed with saturated sodium bicarbonate solution (15 ml), followed by brine (15 ml). The organic layer was dried over Na2SO4 and concentrated in vacuo to afford 5-{4-[4-(3-Pyrrolidin-1-yl-propoxy)-phenyl]-tetrahydro-pyran-4-yl}-4-(toluene-4-sulfonyl)-4,5-dihydro-oxazole as a pale brown foam (500 mg). LRMS ESI+ m/z 513 [MH]+

Workup

  1. additionwas added
  2. customThe solvent was removed in vacuo
  3. washwashed with saturated sodium bicarbonate solution (15 ml)
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c067b92f5c2b40eb8194aaa23d6a5781
Source dataset
uspto-grants-2008_11
Patent number
US07456164B2

Reaction notes

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