Ammonia → HCID 68626787, compound

HRID 1961606Notes

Reaction equation

HRID 1961606 reaction equation
[CH3:1][N:2]([CH3:21])[C:3]([N:5]1[CH2:9][CH:8]2[CH2:10][C:11]([CH:16]3[CH2:20][CH2:19][CH2:18][CH2:17]3)([N:13]=C=O)[CH2:12][CH:7]2[CH2:6]1)=[O:4].N>Cl>[CH3:1][N:2]([CH3:21])[C:3]([N:5]1[CH2:9][CH:8]2[CH2:10][C:11]([NH2:13])([CH:16]3[CH2:17][CH2:18][CH2:19][CH2:20]3)[CH2:12][CH:7]2[CH2:6]1)=[O:4]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 86648342HCID 86648342, compound

Product 1

HCID 68626787HCID 68626787, compoundYield 81.8%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Upon cooling by an ice-water bath, to a solution of 10 mL hydrochloric acid (8 N) was added dropwise 5-cyclopentyl-5-isocyanato-hexahydro-cyclopenta[c]pyrrole-2-carboxylic acid dimethylamide 16e obtained from the above step. Then the ice-water bath was removed and the reaction mixture was reacted at 50° C. for 15 minutes. The reaction was monitored by TLC until the disappearance of the starting materials. The mixture was adjusted to pH>8 with concentrated ammonia and extracted with ethyl acetate. 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-cyclopentyl-hexahydro-cyclopenta[c]pyrrole-2-carboxylic acid dimethylamide 16f (0.18 g, yield 81.8%) as a yellow oil.

Workup

  1. customobtained from the above step
  2. customThen the ice-water bath was removed
  3. customthe reaction mixture was reacted at 50° C. for 15 minutes
  4. extractionextracted with ethyl acetate
  5. dry with materialThe combined organic extracts were dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-bb11013ea9624b1b8c297e30f9d05c06
Source dataset
uspto-grants-2013_04
Patent number
US08415349B2

Reaction notes

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