HCID 57078219, compound → (3S,4S)-3,4-Dimethoxypyrrolidine

HRID 8583Notes

Reaction equation

HRID 8583 reaction equation
[CH3:1][O:2][C@@H:3]1[C@@H:7]([O:8][CH3:9])[CH2:6][N:5](C(OC(C)(C)C)=O)[CH2:4]1>Cl>[CH3:1][O:2][C@@H:3]1[C@@H:7]([O:8][CH3:9])[CH2:6][NH:5][CH2:4]1

Participants

3

Reactant 1

HCID 57078219HCID 57078219, compound

Product 1

HCID 14784825(3S,4S)-3,4-Dimethoxypyrrolidine

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

2.30 g (9.35 mmol; 94% pure) of tert-butyl (3S,4S)-3,4-dimethoxy-1-pyrrolidinecarboxylate (example XVI, step 2) are taken up in 50 ml of hydrochloric acid (4M in dioxane) and stirred at RT overnight. The solvent is removed in vacuo, and the residue is suspended in DCM, mixed with 1N sodium hydroxide solution and stirred at RT for 10 minutes. The phases are separated and the aqueous phase is extracted several times with DCM. The combined organic phases are extracted with saturated aqueous sodium chloride solution, dried and filtered, and the solvent is removed in vacuo. 872 mg (63% of theory) of the product are obtained.

Workup

  1. customThe solvent is removed in vacuo
  2. additionmixed with 1N sodium hydroxide solution
  3. stirringstirred at RT for 10 minutes
  4. customThe phases are separated
  5. extractionthe aqueous phase is extracted several times with DCM
  6. extractionThe combined organic phases are extracted with saturated aqueous sodium chloride solution
  7. customdried
  8. filtrationfiltered
  9. customthe solvent is removed in vacuo
  10. custom872 mg (63% of theory) of the product are obtained

Sources & evidence

ORD record
ord-56e66fdfb1a7426089450f3a51e6ba10
Source dataset
uspto-grants-2006_08
Patent number
US07091198B1

Reaction notes

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