Boron tribromide → HCID 118207320, compound

HRID 1507245Notes

Reaction equation

HRID 1507245 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]([CH3:28])=[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:23]=[CH:24][C:25]([CH3:28])=[CH:26][CH:27]=3)[C:17]2=[O:29])[CH2:3]1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 118207572HCID 118207572, compound

Product 1

HCID 118207320HCID 118207320, compoundYield 12.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

A mixture of 3-(3,3-difluoro-4-(4-methoxyphenyl)piperidin-1-yl)-1-(4-methylbenzyl)pyrrolidin-2-one (230 mg, 0.55 mmol) and 4 mL DCM was cooled to −78° C., followed by the dropwise addition of boron tribromide (0.05 mL, 0.55 mmol). The mixture was then allowed to warm up to rt over 4 h. The reaction was then quenched with 50 mL of 10% aqueous sodium bicarbonate and extracted with 4×50 mL DCM. The combined organic fractions were dried over Na2SO4, filtered, and concentrated. The residue was subjected to preparative HPLC (method B) to afford 28.1 mg 3-(3,3-difluoro-4-(4-hydroxyphenyl)piperidin-1-yl)-1-(4-methylbenzyl)pyrrolidin-2-one as a mixture of 4 diastereomers. LCMS (method N) RT 1.59 min, m/z 401 (M+H+).

Workup

  1. temperatureto warm up to rt over 4 h
  2. customThe reaction was then quenched with 50 mL of 10% aqueous sodium bicarbonate
  3. extractionextracted with 4×50 mL DCM
  4. dry with materialThe combined organic fractions were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b0907203f3c849c2bf001cf23748802f
Source dataset
uspto-grants-2015_12
Patent number
US09221796B2

Reaction notes

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