Tetrahydrofuran → 3-{(1S,5R)-1-[4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hex-3-yl}-1-propanol

HRID 12647

반응식

HRID 12647 반응식
[F:1][C:2]([F:16])([F:15])[C:3]1[CH:8]=[CH:7][C:6]([C@:9]23[CH2:14][C@H:13]2[CH2:12][NH:11][CH2:10]3)=[CH:5][CH:4]=1.[CH2:17]1C[O:20][CH2:19][CH2:18]1>BrCCCO>[F:16][C:2]([F:1])([F:15])[C:3]1[CH:4]=[CH:5][C:6]([C@:9]23[CH2:14][C@H:13]2[CH2:12][N:11]([CH2:17][CH2:18][CH2:19][OH:20])[CH2:10]3)=[CH:7][CH:8]=1

참가 물질

4

반응물 2

HCID 8028TetrahydrofuranHCID 59337591(1S,5R)-1-[4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hexane

생성물 1

HCID 593375943-{(1S,5R)-1-[4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hex-3-yl}-1-propanol

시약·촉매·용매 1

HCID 123083-Bromo-1-propanol용매

실험 절차

To a solution of (1S,5R)-1-[4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hexane (Prep4, 151 mg) in dry THF (3.3 mL), TEA (0.112 mL) and 3-bromo-1-propanol (0.073 mL) were added and the resulting mixture was heated at reflux for 4 hours. After cooling at room temperature it was diluted with EtAcO (20 mL), washed with water, dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude product was purified by a silica SPE cartridge (10 g) eluting with DCM/MeOH from 99/1 to 96/4 to give the title compound as a colourless oil (143 mg).

후처리

  1. temperaturethe resulting mixture was heated
  2. temperatureat reflux for 4 hours
  3. additionwas diluted with EtAcO (20 mL)
  4. washwashed with water
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by a silica SPE cartridge (10 g)
  8. washeluting with DCM/MeOH from 99/1 to 96/4

출처 및 근거

ORD 기록
ord-9b7f790f5e6545a49cac5475acb2be1c
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07727988B2

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