Hydrochloric Acid → Tetrahydro-4H-1,3-dioxolo[4,5-C]pyrrole hydrochloride

HRID 1668686Notes

Reaction equation

HRID 1668686 reaction equation
[O:1]1[CH:5]2[CH2:6][N:7](C(OC(C)(C)C)=O)[CH2:8][CH:4]2[O:3][CH2:2]1.[ClH:16]>ClCCl.C(O)(C)C>[ClH:16].[O:1]1[CH:5]2[CH2:6][NH:7][CH2:8][CH:4]2[O:3][CH2:2]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 59682912Tert-butyl 3,4-methylenedioxypyrrolidine-1-carboxylate

Product 1

HCID 66763181Tetrahydro-4H-1,3-dioxolo[4,5-C]pyrrole hydrochlorideYield 95%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 6344DichloromethaneSolvent

Procedure

tert-Butyl tetrahydro-5H-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylate (19.77 g) was dissolved in dichloromethane (500 mL) and cooled in an ice bath. Cold (from the fridge) HCl in isopropanol (150 mL; 5N) solution was added and the reaction mixture was stirred at ambient temperature for 4 hours. The solvents were evaporated off and the residue triturated under ether. The precipitate was collected by filtration, washed with ether and dried to give tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyrrole hydrochloride (13.18 g; 95%) as a beige solid.

Workup

  1. temperaturecooled in an ice bath
  2. customThe solvents were evaporated off
  3. customthe residue triturated under ether
  4. filtrationThe precipitate was collected by filtration
  5. washwashed with ether
  6. customdried

Sources & evidence

ORD record
ord-698c3ed3107048028d7926893d02d01d
Source dataset
uspto-grants-2011_08
Patent number
US07989460B2

Reaction notes

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