Boron tribromide → (R)-1-[5-(4-chlorophenoxy)pyrazin-2-yl]-5-(3-hydroxyphenyl)pyrrolidin-2-one

HRID 1972246Notes

Reaction equation

HRID 1972246 reaction equation
[Cl:1][C:2]1[CH:28]=[CH:27][C:5]([O:6][C:7]2[N:8]=[CH:9][C:10]([N:13]3[C@@H:17]([C:18]4[CH:23]=[CH:22][CH:21]=[C:20]([O:24]C)[CH:19]=4)[CH2:16][CH2:15][C:14]3=[O:26])=[N:11][CH:12]=2)=[CH:4][CH:3]=1.B(Br)(Br)Br>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][C:7]2[N:8]=[CH:9][C:10]([N:13]3[C@@H:17]([C:18]4[CH:23]=[CH:22][CH:21]=[C:20]([OH:24])[CH:19]=4)[CH2:16][CH2:15][C:14]3=[O:26])=[N:11][CH:12]=2)=[CH:27][CH:28]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 59485648(R)-1-[5-(4-chlorophenoxy)pyrazin-2-yl]-5-(3-methoxyphenyl)pyrrolidin-2-one

Product 1

HCID 59485583(R)-1-[5-(4-chlorophenoxy)pyrazin-2-yl]-5-(3-hydroxyphenyl)pyrrolidin-2-oneYield 100.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of (R)-1-[5-(4-chlorophenoxy)pyrazin-2-yl]-5-(3-methoxyphenyl)pyrrolidin-2-one (286 mg, 0.72 mmol), DCM (10 mL) and BBr3 (1M in DCM, 4 mL) is stirred at room temperature for 1 h. The reaction mixture is then diluted with DCM (120 mL), washed with saturated NaHCO3 (20 mL) and brine (20 mL) and dried over Na2SO4. After concentrating, the residue is purified on silica gel (0-33% ethyl acetate in hexane) to give (R)-1-[5-(4-chlorophenoxy)pyrazin-2-yl]-5-(3-hydroxyphenyl)pyrrolidin-2-one (276 mg, 100%) as a white solid. HPLC-MS calculated for C20H16ClN3O3 (M+H+) 382.09, found 382.10.

Workup

  1. washwashed with saturated NaHCO3 (20 mL) and brine (20 mL)
  2. dry with materialdried over Na2SO4
  3. concentrationAfter concentrating
  4. customthe residue is purified on silica gel (0-33% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-3ced979531644e578809dc8338355e15
Source dataset
uspto-grants-2013_04
Patent number
US08431607B2

Reaction notes

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