Acetic Acid → HCID 86659845, compound

HRID 2402740Notes

Reaction equation

HRID 2402740 reaction equation
S(=O)(=O)(O)O.[CH2:6]([N:13]1[CH2:17][C@@H:16]2[C:18](=[CH2:21])[CH2:19][CH2:20][C@@H:15]2[CH2:14]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(O)(=[O:24])C.[C:26](#[N:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>>[CH2:6]([N:13]1[CH2:17][C@@H:16]2[C@:18]([NH:33][C:26](=[O:24])[C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)([CH3:21])[CH2:19][CH2:20][C@@H:15]2[CH2:14]1)[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 1118Sulfuric AcidHCID 7505BenzonitrileHCID 11629873HCID 11629873, compound

Product 1

HCID 86659845HCID 86659845, compound

Procedure

Sulfuric acid (1.437 mL, 27.0 mmol) was added to a solution of (3aS,6aS)-2-benzyl-4-methyleneoctahydrocyclopenta[c]pyrrole (0.575 g, 2.70 mmol, Example 1) in acetic acid (1.466 mL, 25.6 mmol) and benzonitrile (1.390 mL, 13.48 mmol) at 0° C. The reaction was stirred at room temperature overnight. The reaction mixture was quenched with ice, extracted with dichloromethane, and then purified by silica gel chromatography using 1-10% methanol (2 N ammonia)/dichloromethane as eluent to give the title compounds.

Workup

  1. customThe reaction mixture was quenched with ice
  2. extractionextracted with dichloromethane
  3. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-02b4a6db30ed4228a49b78bcd09d1aba
Source dataset
uspto-grants-2014_08
Patent number
US08796470B2

Reaction notes

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