Methanesulfonyl chloride → Spiro[2.5]oct-5-ene-5-carbonitrile

HRID 1852475Notes

Reaction equation

HRID 1852475 reaction equation
O[CH:2]1[CH2:9][CH2:8][C:5]2([CH2:7][CH2:6]2)[CH2:4][CH:3]1[C:10]#[N:11].CCN(C(C)C)C(C)C.CS(Cl)(=O)=O.C1CCN2C(=NCCC2)CC1>C(Cl)Cl.O>[CH2:6]1[C:5]2([CH2:8][CH2:9][CH:2]=[C:3]([C:10]#[N:11])[CH2:4]2)[CH2:7]1

Participants

7

Reactant 4

HCID 31297Methanesulfonyl chlorideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 81531DiisopropylethylamineHCID 867310116-Hydroxyspiro[2.5]octane-5-carbonitrile

Product 1

HCID 86731012Spiro[2.5]oct-5-ene-5-carbonitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-hydroxyspiro[2.5]octane-5-carbonitrile (110 mg, 0.73 mmol) in DCM (3.6 mL) was added DIPEA (190 mg, 1.4 mmol) followed by the dropwise addition of methanesulfonyl chloride (92 mg, 0.80 mmol). The resulting mixture was stirred at ambient temperature for 3 hours then DBU was added and stirring continued for 16 hours. The mixture was carefully diluted with water and extracted with EtOAc (2×). The combined organic extracts were washed with 1N aqueous HCl, brine, dried over anhydrous Na2SO4, filtered, and concentrated in vacuo to afford the title compound. The residue was carried forward without further purification.

Workup

  1. stirringstirring
  2. waitcontinued for 16 hours
  3. extractionextracted with EtOAc (2×)
  4. washThe combined organic extracts were washed with 1N aqueous HCl, brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3e2a8a746d164666a15bc7ff3f06789d
Source dataset
uspto-grants-2015_02
Patent number
US08962608B2

Reaction notes

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