Hydrochloric Acid → HCID 68626949, compound

HRID 1873552Notes

Reaction equation

HRID 1873552 reaction equation
Cl.[CH3:2][N:3]([CH3:19])[C:4]([N:6]1[CH2:10][CH:9]2[CH2:11][C:12]([CH2:17][CH3:18])([N:14]=C=O)[CH2:13][CH:8]2[CH2:7]1)=[O:5].[OH-].[Na+]>>[CH3:19][N:3]([CH3:2])[C:4]([N:6]1[CH2:10][CH:9]2[CH2:11][C:12]([NH2:14])([CH2:17][CH3:18])[CH2:13][CH:8]2[CH2:7]1)=[O:5]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86648344HCID 86648344, compound

Product 1

HCID 68626949HCID 68626949, compoundYield 71%

Procedure

To a solution of 12 mL hydrochloric acid (8 N) was added 5-ethyl-5-isocyanato-hexahydro-cyclopenta[c]pyrrole-2-carboxylic acid dimethylamide 19e obtained from the above step at room temperature. The reaction mixture was stirred for 30 minutes and adjusted to pH 9-10 with an 8 N aqueous sodium hydroxide solution. The separated aqueous layer was extracted with dichloromethane (30 mL×5). The combined organic extracts were dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain the title compound 5-amino-5-ethyl-hexahydro-cyclopenta[c]pyrrole-2-carboxylic acid dimethylamide 19f (0.3 g, yield 71%) as a colorless oil.

Workup

  1. customobtained from the above step at room temperature
  2. extractionThe separated aqueous layer was extracted with dichloromethane (30 mL×5)
  3. dry with materialThe combined organic extracts were dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-30a354d202604675ba25b5913359f72c
Source dataset
uspto-grants-2012_11
Patent number
US08304411B2

Reaction notes

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