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

HRID 533780노트

반응식

HRID 533780 반응식
[C:1]1([Li])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N:8]12[CH2:15][CH2:14][C:11]([C:16]([O:18]CC)=O)([CH2:12][CH2:13]1)[CH2:10][CH2:9]2>C1COCC1>[N:8]12[CH2:9][CH2:10][C:11]([C:16]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[OH:18])([CH2:12][CH2:13]1)[CH2:14][CH2:15]2

참가 물질

4

반응물 2

HCID 573424Ethyl 1-azabicyclo(2.2.2)octane-4-carboxylateHCID 178506676HCID 178506676, 화합물

생성물 1

HCID 239923851-Azabicyclo[2.2.2]oct-4-yl(diphenyl)methanol수율 32.7%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of phenyllithium (1.5-1.7 M in 70 cyclohexane/30 ether, 20.0 mL, 32 mmol) was chilled down to −30° C. under Ar. Ethyl 1-azabicyclo[2.2.2]octane-4-carboxylate (1.51 g, 8.23 mmol) in THF (20 mL) was slowly added to the reaction mixture at −30° C. over 25 min. The reaction was allowed to warm up to room temperature over 16 h. The reaction was quenched with H2O and then evaporated to dryness under vacuum. H2O and EtOAc were added, causing a white solid to crash out. This solid was filtered off, to give the title compound (0.79 g). The aqueous phase was further extracted with EtOAc, the combined organic layers were dried over MgSO4, filtered, and concentrated under vacuum. The crude product was treated with EtOAc and hexane and filtered to yield more of the title compound (0.67 g). Total yield (1.46 g, 60.7%). EI-MS m/z 294(M+H+) Rt (1.37 min).

후처리

  1. customThe reaction was quenched with H2O
  2. customevaporated to dryness under vacuum
  3. additionH2O and EtOAc were added
  4. filtrationThis solid was filtered off

출처 및 근거

ORD 기록
ord-3fa8ab73439f4c2ba77435925afb8f20
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08853404B2

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