Boron tribromide → HCID 118207292, compound

HRID 1507254Notes

Reaction equation

HRID 1507254 reaction equation
[F:1][C:2]1([F:30])[CH:7]([C:8]2[CH:13]=[CH:12][C:11]([O:14]C)=[CH:10][CH:9]=2)[CH2:6][CH2:5][N:4]([CH:16]2[CH2:20][CH2:19][N:18]([CH2:21][C:22]3[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=3)[C:17]2=[O:29])[CH2:3]1.B(Br)(Br)Br>C(Cl)Cl>[F:30][C:2]1([F:1])[CH:7]([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)[CH2:6][CH2:5][N:4]([CH:16]2[CH2:20][CH2:19][N:18]([CH2:21][C:22]3[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=3)[C:17]2=[O:29])[CH2:3]1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 118207364HCID 118207364, compound

Product 1

HCID 118207292HCID 118207292, compoundYield 17.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(3,3-difluoro-4-(4-methoxyphenyl)piperidin-1-yl)-1-(4-fluorobenzyl)pyrrolidin-2-one (200 mg, 0.48 mmol, mixture of diastereomers from step D) in DCM (15 mL) at −10° C. was added boron tribromide (0.05 mL, 0.48 mmol) and the reaction mixture was stirred under nitrogen for one hour. The mixture was then diluted with a satd. sodium bicarbonate solution and extracted with 100 mL of DCM. The organic layer was separated, dried over Na2SO4, filtered, and evaporated under reduced pressure. The residue was purified via preparative HPLC (method D) to yield 3-(3,3-difluoro-4-(4-hydroxyphenyl)-piperidin-1-yl)-1-(4-fluorobenzyl)pyrrolidin-2-one (mixture of 4 diastereomers, 34 mg, 17% yield). LCMS (method N) RT 1.497 min, m/z 405.0 (M+H+).

Workup

  1. additionThe mixture was then diluted with a satd
  2. extractionsodium bicarbonate solution and extracted with 100 mL of DCM
  3. customThe organic layer was separated
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customThe residue was purified via preparative HPLC (method D)

Sources & evidence

ORD record
ord-69cbc941b31440e8820c9c6236c5559b
Source dataset
uspto-grants-2015_12
Patent number
US09221796B2

Reaction notes

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