Hydrochloric Acid → HCID 2237132, compound

HRID 344231Notes

Reaction equation

HRID 344231 reaction equation
[C:1]1([C@@H:7]([N:9]2[C:13](=O)[CH2:12][C@H:11]([C:15]([NH2:17])=O)[CH2:10]2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+].S(=O)(=O)(O)O.Cl>O1CCCC1>[NH2:17][CH2:15][C@H:11]1[CH2:12][CH2:13][N:9]([C@H:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH3:8])[CH2:10]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1118Sulfuric AcidHCID 4311764Sodium borohydrideHCID 54306395(3S)-5-Oxo-1-[(1S)-1-phenylethyl]-3-pyrrolidinecarboxamide

Product 1

HCID 2237132HCID 2237132, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(3S)-1-((S)-1-Phenylethyl)-5-oxo-3-pyrrolidinecarboxamide (150 g) was dissolved in tetrahydrofuran (2.5 l), and sodium borohydride (138 g) was added with stirring. Conc. sulfuric acid (130 ml) was dropwise added under ice-cooling. The mixture was stirred for 1 hr at room temperature, and further at refluxing temperature for 10 hr. 6N Hydrochloric acid (300 ml) was dropwise added under ice-cooling, and the mixture was stirred at refluxing temperature for 4 hr. The solvent was evaporated under reduced pressure, a 3N sodium hydroxide solution was added to make same alkaline, and the mixture was extracted with chloroform. The extract was dried over magnesium sulfate, concentrated under reduced pressure and distilled under reduced pressure to give 95 g of (3R)-3-aminomethyl-1-((S)-1-phenylethyl)pyrrolidine.

Workup

  1. temperaturecooling
  2. stirringThe mixture was stirred for 1 hr at room temperature
  3. temperaturefurther at refluxing temperature for 10 hr
  4. temperaturecooling
  5. stirringthe mixture was stirred
  6. temperatureat refluxing temperature for 4 hr
  7. customThe solvent was evaporated under reduced pressure
  8. additiona 3N sodium hydroxide solution was added
  9. extractionthe mixture was extracted with chloroform
  10. dry with materialThe extract was dried over magnesium sulfate
  11. concentrationconcentrated under reduced pressure
  12. distillationdistilled under reduced pressure

Sources & evidence

ORD record
ord-f84f0933de48498183236ebbe4e1402b
Source dataset
uspto-grants-1999_01
Patent number
US05864039

Reaction notes

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