Ammonia → HCID 68626800, compound

HRID 1961602Notes

Reaction equation

HRID 1961602 reaction equation
[CH3:1][N:2]([CH3:23])[C:3]([N:5]1[CH2:9][CH:8]2[CH2:10][C:11]([CH2:16][CH:17]3[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]3)([N:13]=C=O)[CH2:12][CH:7]2[CH2:6]1)=[O:4].N>Cl>[CH3:23][N:2]([CH3:1])[C:3]([N:5]1[CH2:9][CH:8]2[CH2:10][C:11]([NH2:13])([CH2:16][CH:17]3[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]3)[CH2:12][CH:7]2[CH2:6]1)=[O:4]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 86648341HCID 86648341, compound

Product 1

HCID 68626800HCID 68626800, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Upon cooling by an ice-water bath, to a solution of 10 mL of hydrochloric acid (8 N) was added dropwise 5-cyclohexylmethyl-5-isocyanato-hexahydro-cyclopenta[c]pyrrole-2-carboxylic acid dimethylamide 15e (0.65 g, 2.03 mmol). Then the ice-water bath was removed. The reaction mixture was reacted at 50° C. for 20 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 (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 5-amino-5-cyclohexylmethyl-hexahydro-cyclopenta[c]pyrrole-2-carboxylic acid dimethylamide 15f (0.5 g, yield 84%) as a grey oil.

Workup

  1. customThen the ice-water bath was removed
  2. customThe reaction mixture was reacted at 50° C. for 20 minutes
  3. extractionextracted with ethyl acetate (30 mL×5)
  4. dry with materialThe combined organic extracts were dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-e9b9780e48404c73b45f4c4054aca826
Source dataset
uspto-grants-2013_04
Patent number
US08415349B2

Reaction notes

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