Ammonium Chloride → HCID 21892325, compound

HRID 720469Notes

Reaction equation

HRID 720469 reaction equation
Cl[C:2]1(Cl)[CH:6]2[N:7]([C:10]([O:12][CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[O:11])[CH2:8][CH2:9][CH:5]2[CH2:4][C:3]1=[O:20].[Cl-].[NH4+]>CO.[Zn]>[O:20]=[C:3]1[CH2:2][CH:6]2[N:7]([C:10]([O:12][CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[O:11])[CH2:8][CH2:9][CH:5]2[CH2:4]1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 21892766HCID 21892766, compound

Product 1

HCID 21892325HCID 21892325, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 887MethanolSolvent

Procedure

Benzyl 6,6-dichloro-5-oxohexahydrocyclopenta[b]pyrrole-1(2H)-carboxylate (3.87 g, 11.8 mmol), prepared as described in Tetrahedron Lett. (1997), 38, 1869–1872, in MeOH (60 mL) at 0° C. was treated with solid ammonium chloride (6.32 g, 118 mmol) followed by zinc duct (Aldrich; 3.09 g, 47.2 mmol). After stirring at room temperature for 1 hour, the reaction mixture was filtered and the filtrate concentrated under reduced pressure. The residue was purified by chromatography (SiO2, 40% EtOAc/hexanes) to provide 2.57 g (84%) of the title compound. MS (DCI/NH3) m/z 260 (M+H)+.

Workup

  1. filtrationthe reaction mixture was filtered
  2. concentrationthe filtrate concentrated under reduced pressure
  3. customThe residue was purified by chromatography (SiO2, 40% EtOAc/hexanes)

Sources & evidence

ORD record
ord-d6e7f62a04004882ad560efd1eab55bf
Source dataset
uspto-grants-2006_11
Patent number
US07135484B2

Reaction notes

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