Boron tribromide → 1-[4-(5-Hydroxypyrimidin-2-yl)phenyl]-4-pentylbicyclo[2.2.2]octane

HRID 635137Notes

Reaction equation

HRID 635137 reaction equation
B(Br)(Br)Br.C([O:12][C:13]1[CH:14]=[N:15][C:16]([C:19]2[CH:24]=[CH:23][C:22]([C:25]34[CH2:32][CH2:31][C:28]([CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])([CH2:29][CH2:30]3)[CH2:27][CH2:26]4)=[CH:21][CH:20]=2)=[N:17][CH:18]=1)C1C=CC=CC=1>ClCCl>[OH:12][C:13]1[CH:18]=[N:17][C:16]([C:19]2[CH:20]=[CH:21][C:22]([C:25]34[CH2:32][CH2:31][C:28]([CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])([CH2:29][CH2:30]3)[CH2:27][CH2:26]4)=[CH:23][CH:24]=2)=[N:15][CH:14]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 699647591-[4-(5-Benzyloxypyrimidin-2-yl) phenyl]-4-pentylbicyclo[2.2.2]octane

Product 1

HCID 212577621-[4-(5-Hydroxypyrimidin-2-yl)phenyl]-4-pentylbicyclo[2.2.2]octaneYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A one molar solution of boron tribromide (120 cm3) is added dropwise to a solution 1-[4-(5-benzyloxypyrimidin-2-yl) phenyl]-4-pentylbicyclo[2.2.2]octane (38.5 g, 100 mmol) in dichloromethane (200 cm3) and cooled using an ice bath. The reaction is stirred overnight at room temperature and then poured onto an ice/water mixture (500 g). The organic layer is separated off and the aqueous layer extracted with dichloromethane (3×100 cm3). The combined organic layers are washed with water (500 cm3), dilute potassium carbonate (200 cm3) and once again with water (500 cm3) then dried (MgSO4), filtered and evaporated. The residue is purified by column chromatography (flash) on silica gel using a 97:3 dichloromethane/methanol mixture as eluent followed by recrystallisation from ethyl acetate to give the 1-[4-(5-hydroxypyrimidin-2-yl)phenyl]-4-pentylbicyclo[2.2.2]octane (14.7 g, 50%).

Workup

  1. temperaturecooled
  2. customThe organic layer is separated off
  3. extractionthe aqueous layer extracted with dichloromethane (3×100 cm3)
  4. washThe combined organic layers are washed with water (500 cm3), dilute potassium carbonate (200 cm3) and once again with water (500 cm3)
  5. dry with materialthen dried (MgSO4)
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue is purified by column chromatography (flash) on silica gel using a 97:3 dichloromethane/methanol mixture as eluent
  9. customfollowed by recrystallisation from ethyl acetate

Sources & evidence

ORD record
ord-d69c17a6b8f2415f93a2bd3998133bcf
Source dataset
uspto-grants-2001_02
Patent number
US06187393B1

Reaction notes

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