Hydrochloric Acid → 334999-32-5

HRID 1267532Notes

Reaction equation

HRID 1267532 reaction equation
[N:1]([C@H:4]1[CH2:8][N:7]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[C@H:6]([C:16]([O:18][CH3:19])=[O:17])[CH2:5]1)=[N+]=[N-].[ClH:20]>[Pd].C(O)C>[Cl-:20].[NH3+:1][C@H:4]1[CH2:8][N:7]([C:9]([O:11][C:12]([CH3:13])([CH3:14])[CH3:15])=[O:10])[C@H:6]([C:16]([O:18][CH3:19])=[O:17])[CH2:5]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 11369242(2S,4R)-4-Azido-1,2-pyrrolidinedicarboxylic Acid 1-(1,1-Dimethylethyl) 2-Methyl Ester

Product 1

HCID 86586343334999-32-5

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Palladium on carbon (10%, 0.5 g) was added to a solution of 1-(tert-butyl)-2-methyl(2S,4R)-4-azidotetrahydro-1H-1,2-pyrroledicarboxylate (5) (0.81 g, 3.0 mmol) in 2% v/v hydrochloric acid in ethanol (8 mL). The reaction mixture was evacuated and purged with nitrogen (three times), then placed under an atmosphere of hydrogen and vigorously stirred at room temperature overnight. The mixture was filtered through a pad of Celite and evaporated under reduced pressure to give the crude product. This was triturated with diethyl ether at 0° C. and the resulting slurry was filtered, washed with ice-cold diethyl ether and dried under vacuum. The title salt (6) was obtained in quantitative yield:

Workup

  1. customThe reaction mixture was evacuated
  2. custompurged with nitrogen (three times)
  3. filtrationThe mixture was filtered through a pad of Celite
  4. customevaporated under reduced pressure
  5. customto give the crude product
  6. customThis was triturated with diethyl ether at 0° C.
  7. filtrationthe resulting slurry was filtered
  8. washwashed with ice-cold diethyl ether
  9. customdried under vacuum

Sources & evidence

ORD record
ord-abb189c00b2c4c79bd6850f65a139024
Source dataset
uspto-grants-2003_04
Patent number
US06552016B1

Reaction notes

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