Hydrochloric Acid → trans-3-Amino-4-methoxypyrrolidine dihydrochloride

HRID 358900Notes

Reaction equation

HRID 358900 reaction equation
[ClH:1].[NH2:2][CH:3]1[CH:7]([O:8][CH3:9])[CH2:6][N:5](C(OC(C)(C)C)=O)[CH2:4]1>C(O)C>[ClH:1].[ClH:1].[NH2:2][C@H:3]1[C@H:7]([O:8][CH3:9])[CH2:6][NH:5][CH2:4]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 20067140tert-Butyl 3-amino-4-methoxypyrrolidine-1-carboxylate

Product 1

HCID 67925434trans-3-Amino-4-methoxypyrrolidine dihydrochloride

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

6.3 ml of 6N aqueous hydrochloric acid were added to a solution of 0.4 g (0.0019 mole) of 3-amino-1-t-butoxycarbonyl-4-methoxypyrrolidine [prepared as described in Step (3) above] dissolved in 20 ml of ethanol, and the mixture was heated under reflux for 1.5 hours, after which the solvent was removed by evaporation under reduced pressure. The residue was washed with a 1:9 by volume mixture of ethanol and ethyl acetate to give 0.34 g of trans-3-amino-4-methoxypyrrolidine dihydrochloride as a colorless powder, melting at 248°~258° C. (with decomposition).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1.5 hours
  3. customafter which the solvent was removed by evaporation under reduced pressure
  4. washThe residue was washed with a 1:9 by volume mixture of ethanol and ethyl acetate

Sources & evidence

ORD record
ord-995b5ec61da5453f84f27d08bd551762
Source dataset
uspto-grants-1991_03
Patent number
US04997943

Reaction notes

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