Ethyl 1-azabicyclo(2.2.2)octane-4-carboxylate → 1-Azabicyclo[2.2.2]oct-4-yl(di-2-thienyl)methanol

HRID 533804ノート

反応式

HRID 533804 の反応式
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[Li].[N:7]12[CH2:14][CH2:13][C:10]([C:15]([O:17]CC)=O)([CH2:11][CH2:12]1)[CH2:9][CH2:8]2>C1COCC1>[N:7]12[CH2:8][CH2:9][C:10]([C:15]([C:2]3[S:1][CH:5]=[CH:4][CH:3]=3)([C:2]3[S:1][CH:5]=[CH:4][CH:3]=3)[OH:17])([CH2:11][CH2:12]1)[CH2:13][CH2:14]2

参加物

4

反応物 2

HCID 573424Ethyl 1-azabicyclo(2.2.2)octane-4-carboxylateHCID 178418439HCID 178418439、化合物

生成物 1

HCID 688655991-Azabicyclo[2.2.2]oct-4-yl(di-2-thienyl)methanol収率 59.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of 2-thienyllithium (1.0M in THF, 9.10 mL, 9.10 mmol) was chilled down to −30° C. under Ar. Ethyl 1-azabicyclo[2.2.2]octane-4-carboxylate (0.4196 g, 2.289 mmol) in THF (8 mL) was slowly added to the reaction mixture over 20 min. The reaction was allowed to warm up to room temperature over 16 h. The reaction was quenched with water and then evaporated to dryness. H2O and DCM were added, causing a light brown solid to crash out. This solid was filtered off to give the title compound (0.4161 g, 59.5%). EI-MS m/z 306(M+H+) Rt (1.35 min).

後処理

  1. customThe reaction was quenched with water
  2. customevaporated to dryness
  3. additionH2O and DCM were added
  4. filtrationThis solid was filtered off

出典と根拠

ORDレコード
ord-38c45784d6454158b87174f507390329
出典データセット
uspto-grants-2014_10
特許番号
US08853404B2

反応ノート

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