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

HRID 12647

Reaction equation

HRID 12647 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 123083-Bromo-1-propanolSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-9b7f790f5e6545a49cac5475acb2be1c
Source dataset
uspto-grants-2010_06
Patent number
US07727988B2

Linked notes

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