Ethyl 1-azabicyclo(2.2.2)octane-4-carboxylate → 1-Azabicyclo[2.2.2]oct-4-yl[bis(3-methylphenyl)]methanol

HRID 1782481ノート

反応式

HRID 1782481 の反応式
[CH3:1][C:2]1[CH:3]=[C:4]([Mg]Br)[CH:5]=[CH:6][CH:7]=1.[N:10]12[CH2:17][CH2:16][C:13]([C:18]([O:20]CC)=O)([CH2:14][CH2:15]1)[CH2:12][CH2:11]2>C1COCC1>[N:10]12[CH2:11][CH2:12][C:13]([C:18]([C:6]3[CH:5]=[CH:4][CH:3]=[C:2]([CH3:1])[CH:7]=3)([C:6]3[CH:5]=[CH:4][CH:3]=[C:2]([CH3:1])[CH:7]=3)[OH:20])([CH2:14][CH2:15]1)[CH2:16][CH2:17]2

参加物

4

反応物 2

HCID 573424Ethyl 1-azabicyclo(2.2.2)octane-4-carboxylateHCID 178425413HCID 178425413、化合物

生成物 1

HCID 689628891-Azabicyclo[2.2.2]oct-4-yl[bis(3-methylphenyl)]methanol収率 69.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of 3-methylphenylmagnesiumbromide (1.0 M in THF, 3.3 mL, 3.3 mmol) was chilled down to 0° C. under Ar. Ethyl 1-azabicyclo[2.2.2]octane-4-carboxylate (0.1484 g, 0.810 mmol) in THF (4 mL) was slowly added to the reaction mixture at 0° C. over 20 min. The reaction was allowed to warm up to room temperature and then heated at 60° C. for 16 h. The reaction was chilled in an ice bath, quenched with saturated NH4Cl, and concentrated under vacuum. The resulting residue was treated with H2O and extracted with EtOAc. The combined organic layers were dried with MgSO4, filtered, and concentrated under vacuum to yield the desired product (0.1806 g, 69.4%). EI-MS m/z 322(M+H+) Rt (1.54 min).

後処理

  1. temperatureheated at 60° C. for 16 h
  2. temperatureThe reaction was chilled in an ice bath
  3. customquenched with saturated NH4Cl
  4. concentrationconcentrated under vacuum
  5. additionThe resulting residue was treated with H2O
  6. extractionextracted with EtOAc
  7. dry with materialThe combined organic layers were dried with MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated under vacuum

出典と根拠

ORDレコード
ord-127f06aa4fd943f5bc20ab4e2d682fbf
出典データセット
uspto-grants-2009_03
特許番号
US07498440B2

反応ノート

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