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

HRID 1852475ノート

反応式

HRID 1852475 の反応式
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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-3e2a8a746d164666a15bc7ff3f06789d
出典データセット
uspto-grants-2015_02
特許番号
US08962608B2

反応ノート

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