Water → HCID 20115238, compound

HRID 558127Notes

Reaction equation

HRID 558127 reaction equation
[BH4-].[Na+].[Br:3][C:4]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:5]=1[C:11]1[CH2:12][CH2:13][CH2:14][N:15]=1.O.[OH-].[Na+]>CO.C(O)(=O)C>[Br:3][C:4]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:5]=1[CH:11]1[CH2:12][CH2:13][CH2:14][NH:15]1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 574450765-(2-bromo-4-fluorophenyl)-3,4-dihydro-2H-pyrrole

Product 1

HCID 20115238HCID 20115238, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 10129899Acetic acid methanolSolvent

Procedure

Add sodium tetrahydroborate (146 mg, 3.7 mmol) to a solution of 5-(2-bromo-4-fluorophenyl)-3,4-dihydro-2H-pyrrole (420 mg, 1.73 mmol) in methanol-acetic acid (saturated; 10 mL) mixture at −40° C. After warming up to RT, add water (10 mL) and make the solution basic with a NaOH solution (2 N). Extract the solution with DCM, wash the organic solution with aqueous saturated sodium chloride, dry over potassium carbonate, and remove the organic solvent to give the title compound (300 mg, 71%). MS (ES) m/z 236 [M+1]+.

Workup

  1. extractionExtract the solution with DCM
  2. washwash the organic solution with aqueous saturated sodium chloride
  3. dry with materialdry over potassium carbonate
  4. customremove the organic solvent

Sources & evidence

ORD record
ord-8c8e5aeb3e304a5ebdf2f07233827352
Source dataset
uspto-grants-2011_11
Patent number
US08063035B2

Reaction notes

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