1,4-Dibromobutane → (R)-2-phenyl-2-(pyrrolidin-1-yl)acetic acid

HRID 923396

Reaction equation

HRID 923396 reaction equation
[NH2:1][C@H:2]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:3]([OH:5])=[O:4].Br[CH2:13][CH2:14][CH2:15][CH2:16]Br.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C>[C:6]1([C@@H:2]([N:1]2[CH2:16][CH2:15][CH2:14][CH2:13]2)[C:3]([OH:5])=[O:4])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 80561,4-DibromobutaneHCID 10340Sodium CarbonateHCID 70134Phenylglycine, D-

Product 1

HCID 1091376(R)-2-phenyl-2-(pyrrolidin-1-yl)acetic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To (R)-2-amino-2-phenylacetic acid (1.0 g, 6.62 mmol), 1,4-dibromobutane (1.57 g, 0.727 mmol) and sodium carbonate (2.103 g, 19.85 mmol) was added ethanol (40 mL) and the resultant mixture heated at 100° C. for 65 hours. After cooling, the resultant solid was removed by filtration and washed with ethanol. The filtrate was concentrated, and then dissolved in ethanol then a solution of 4N aqueous hydrochloric acid added until the pH of the solution was 3. The resultant solid was removed and discarded. The filtrate was concentrated and purified by reversed phase chromatography (C18), eluting with 10-100% acetonitrile in water (0.1% TFA) to give the title compound. MS (ESI) m/z 206 (M+H)+.

Workup

  1. temperatureAfter cooling
  2. customthe resultant solid was removed by filtration
  3. washwashed with ethanol
  4. concentrationThe filtrate was concentrated
  5. dissolutiondissolved in ethanol
  6. additiona solution of 4N aqueous hydrochloric acid added until the pH of the solution
  7. customThe resultant solid was removed
  8. concentrationThe filtrate was concentrated
  9. custompurified by reversed phase chromatography (C18)
  10. washeluting with 10-100% acetonitrile in water (0.1% TFA)

Sources & evidence

ORD record
ord-7ff40c0637274244aa335e14f625a63f
Source dataset
uspto-grants-2016_03
Patent number
US09278922B2

Linked notes

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