Ethanol → HCID 14975361, compound

HRID 1460743Notes

Reaction equation

HRID 1460743 reaction equation
OS(O)(=O)=O.[C:6]1([C@H:12]([N:14]2[CH2:18][CH2:17][C@H:16]([CH2:19][C:20]#N)[CH2:15]2)[CH3:13])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[OH-:22].[Na+].[CH3:24][CH2:25][OH:26]>>[C:6]1([C@H:12]([N:14]2[CH2:18][CH2:17][C@H:16]([CH2:19][C:20]([O:26][CH2:25][CH3:24])=[O:22])[CH2:15]2)[CH3:13])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 4

HCID 702Ethanol2×HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 14485385HCID 14485385, compound

Product 1

HCID 14975361HCID 14975361, compoundYield 73%

Procedure

To a mixture of EtOH (30 mL) and H2SO4 (15 mL) at 25° C. was added (3R)-1-[(R)-1-phenylethyl]-3-(cyanomethyl)pyrrolidine 3a (7.5 g, 35 mmol) in EtOH (5 mL). The solution was heated at reflux for 7 hours, cooled, and the volume reduced by approximately one-half under reduced pressure. The residue was made basic with NaOH and extracted with EtOAc. The organic layer was dried, concentrated, and the residue distilled (bulb to bulb) to provide 4a (6.7 g, 73%); bp 120°-130° C. (0.1-0.2 mm).

Workup

  1. temperatureThe solution was heated
  2. temperatureat reflux for 7 hours
  3. temperaturecooled
  4. extractionextracted with EtOAc
  5. customThe organic layer was dried
  6. concentrationconcentrated
  7. distillationthe residue distilled (bulb to bulb)

Sources & evidence

ORD record
ord-113fd8c738a44ffdba188092cb71753a
Source dataset
uspto-grants-1991_12
Patent number
US05072001

Reaction notes

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