Carbon Tetrachloride → HCID 21963817, compound

HRID 2212082Notes

Reaction equation

HRID 2212082 reaction equation
O[CH:2]1[CH:7]2[CH2:8][CH:4]([CH2:5][N:6]2[CH2:9][CH2:10][CH2:11][C:12]([CH3:23])([S:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)(=[O:16])=[O:15])[CH3:13])[CH2:3]1.[C-:24]#[N:25].[K+].C1OCCOCCOCCOCCOCCOC1.C(P(CCCC)CCCC)CCC.C(Cl)(Cl)(Cl)Cl>C(#N)C>[C:24]([CH:2]1[CH:7]2[CH2:8][CH:4]([CH2:5][N:6]2[CH2:9][CH2:10][CH2:11][C:12]([CH3:23])([S:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)(=[O:16])=[O:15])[CH3:13])[CH2:3]1)#[N:25]

Participants

7

Reactant 5

HCID 5943Carbon TetrachlorideHCID 9032Potassium CyanideHCID 13831TributylphosphineHCID 2855718-Crown-6HCID 21963776HCID 21963776, compound

Product 1

HCID 21963817HCID 21963817, compoundYield 58.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

6-Hydroxy-2-[4-methyl-4-(phenylsulfonyl)pentyl]-2-azabicyclo[2.2.1]heptane (1 g, 2.97 mmol), potassium cyanide (386 mg, 6 mmol) and 18-crown-6 (78 mg, cat.) were suspended in acetonitrile and the mixture was cooled in ice-water. Tri-n-butylphosphine (1.2 ml, 5 mmol) was added followed by dropwise addition of carbon tetrachloride (0.57 ml, 6 mmol). The mixture was allowed to stir at room temperature for 12 h. The combined organic extracts were washed with brine, dried (MgSO4) and evaporated in vacuo. The residue was purified by column chromatography on silica using a gradient elution of 10–100% ethyl acetate in i-hexane, to give the product (600 mg, 58%) as an oil which crystallised on standing.

Workup

  1. washThe combined organic extracts were washed with brine
  2. dry with materialdried (MgSO4)
  3. customevaporated in vacuo
  4. customThe residue was purified by column chromatography on silica using
  5. washa gradient elution of 10–100% ethyl acetate in i-hexane

Sources & evidence

ORD record
ord-1ebf1a338fc64dd28223dafc30e5337b
Source dataset
uspto-grants-2006_09
Patent number
US07101892B2

Reaction notes

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