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

HRID 1782479노트

반응식

HRID 1782479 반응식
[F: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]([F:1])[CH:7]=3)([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=3)[OH:20])([CH2:14][CH2:15]1)[CH2:16][CH2:17]2

참가 물질

4

반응물 2

HCID 573424Ethyl 1-azabicyclo(2.2.2)octane-4-carboxylateHCID 178505773HCID 178505773, 화합물

생성물 1

HCID 689587571-Azabicyclo[2.2.2]oct-4-yl[bis(3-fluorophenyl)]methanol수율 76.7%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of 3-fluorophenylmagnesiumbromide (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 (0.1756 g, 0.958 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 (0.242 g, 76.7%). EI-MS m/z 330(M+H+) Rt (1.45 min).

후처리

  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

출처 및 근거

ORD 기록
ord-bc6c0b11e9a9404d8d06af211e7a6c21
출처 데이터셋
uspto-grants-2009_03
특허 번호
US07498440B2

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