Acetic Acid → 1-(3-(4-Bromophenyl)propyl)pyrrolidine

HRID 1916579Notes

Reaction equation

HRID 1916579 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH:10]=O)=[CH:4][CH:3]=1.[NH:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1.C(O)(=O)C.[BH3-]C#N.[Na+]>CO.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][N:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 31268PyrrolidineHCID 5003444Sodium cyanoborohydrideHCID 114812883-(4-Bromophenyl)propanal

Product 1

HCID 248235691-(3-(4-Bromophenyl)propyl)pyrrolidine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of 1.03 g (4.82 mmol) 3-(4-bromo-phenyl)-propionaldehyde and 0.41 mL (4.82 mmol) pyrrolidine in 50 mL MeOH is adjusted to pH 4-5 with glacial acetic acid. Then 400 mg (6.05 mmol) NaBH3CN are added batchwise and the reaction is stirred for 3 days at RT. The reaction solution is diluted with 30 mL water and the aqueous phase is extracted with 50 mL EtOAc. The organic phase is dried over Na2SO4 and the solvent is eliminated i.vac. Further purification is carried out by column chromatography on silica gel (EtOAc/MeOH/NH3 9:1:0.1).

Workup

  1. extractionthe aqueous phase is extracted with 50 mL EtOAc
  2. dry with materialThe organic phase is dried over Na2SO4
  3. customFurther purification

Sources & evidence

ORD record
ord-e5414667fb264f29a7e213dbd0fcc68e
Source dataset
uspto-grants-2013_12
Patent number
US08618132B2

Reaction notes

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