Potassium Carbonate → HCID 17756388, compound

HRID 491595Notes

Reaction equation

HRID 491595 reaction equation
[Cl:1][C:2]1[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][C:3]=1[O:4][CH2:5][C@@H:6]1[CH2:10][CH2:9][CH2:8][NH:7]1.Cl[Sn]Cl.[C:21]([O-])([O-])=O.[K+].[K+]>CCO>[Cl:1][C:2]1[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][C:3]=1[O:4][CH2:5][C@@H:6]1[CH2:10][CH2:9][CH2:8][N:7]1[CH3:21]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 24479Stannous ChlorideHCID 17755967(2S)-2-[(2-Chloro-5-nitrophenoxy)methyl]pyrrolidine

Product 1

HCID 17756388HCID 17756388, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(S)-2-(2-Chloro-5-nitro-phenoxymethyl)-pyrrolidine (3.42 g, 12.63 mmol) and SnCl2 (7.19 g, 37.9 mmol) in 45 mL EtOH were heated at 75° C. for 11 h. The reaction was treated with about 15 mL 1 N K2CO3 (aq) and stirred 40 min. The suspension was filtered through Celite and concentrated down to aqueous, which was then diluted with EtOAc and 1 N NaOH (aq). The layers were separated, and the organic layer was washed twice with 1 N NaOH and once with mix of brine and 1 N NaOH. The aqueous layers were extracted twice with fresh EtOAc. The combined organic layers were dried over sodium sulfate, filtered, and concentrated down to dryness to yield the title compound as a brown solid.

Workup

  1. filtrationThe suspension was filtered through Celite
  2. concentrationconcentrated down to aqueous, which
  3. additionwas then diluted with EtOAc and 1 N NaOH (aq)
  4. customThe layers were separated
  5. washthe organic layer was washed twice with 1 N NaOH
  6. additiononce with mix of brine and 1 N NaOH
  7. extractionThe aqueous layers were extracted twice with fresh EtOAc
  8. dry with materialThe combined organic layers were dried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated down to dryness

Sources & evidence

ORD record
ord-d21d4a5b64d741e3bf38251270924748
Source dataset
uspto-grants-2009_05
Patent number
US07531553B2

Reaction notes

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