Diethyl Ether → 8-Thiabicyclo[3.2.1]octane-3-carbonitrile

HRID 900764Notes

Reaction equation

HRID 900764 reaction equation
C(O[K])(C)(C)C.[CH:7]12[S:14][CH:11]([CH2:12][CH2:13]1)[CH2:10][C:9](=O)[CH2:8]2.S([CH2:26][N+:27]#[C-])(C1C=CC(C)=CC=1)(=O)=O.CCOCC>CC(O)(C)C.COCCOC.COCCOC>[CH:7]12[S:14][CH:11]([CH2:12][CH2:13]1)[CH2:10][CH:9]([C:26]#[N:27])[CH2:8]2

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 161915Tosylmethyl isocyanideHCID 2750548-Thiabicyclo(3.2.1)octan-3-oneHCID 178418922HCID 178418922, compound

Product 1

HCID 692908968-Thiabicyclo[3.2.1]octane-3-carbonitrile

Reagents, catalysts & solvents 2

HCID 80711,2-DimethoxyethaneSolventHCID 86596206tert butanol DMESolvent

Procedure

A solution of tert-BuOK (2.41 g, 21.52 mmol) in t-BuOH/DME 1:2 (24 ml) was added at 0° C. to a solution of 8-thiabicyclo[3.2.1]octan-3-one (1.53 g, 10.75 mmol) and tosylmethyl isocyanide (2.3 g, 11.83 mmol) in DME (20 ml). The solution was stirred for 3 hours at room temperature. After addition of ether, the mixture was washed with a saturated aqueous NaHCO3 solution, dried over MgSO4 and evaporated. After purification by chromatography on silica gel (hexane/AcOEt 85/15), 8-thiabicyclo[3.2.1]octane-3-carbonitrile was obtained as a colorless oil (1.03 g, 63%).

Workup

  1. washthe mixture was washed with a saturated aqueous NaHCO3 solution
  2. dry with materialdried over MgSO4
  3. customevaporated
  4. customAfter purification by chromatography on silica gel (hexane/AcOEt 85/15)

Sources & evidence

ORD record
ord-1dc3e5dc35624bc981b1c2085ffd3cd0
Source dataset
uspto-grants-2008_04
Patent number
US07361668B2

Reaction notes

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