Hydrochloric Acid → 3-((Cyclopropylmethoxy)methyl)pyrrolidine

HRID 401802Notes

Reaction equation

HRID 401802 reaction equation
[CH:1]1([CH2:4][O:5][CH2:6][CH:7]2[CH2:11][CH2:10][N:9](C(OC(C)(C)C)=O)[CH2:8]2)[CH2:3][CH2:2]1.Cl>C(O)(C)C>[CH:1]1([CH2:4][O:5][CH2:6][CH:7]2[CH2:11][CH2:10][NH:9][CH2:8]2)[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57732113Tert-butyl 3-((cyclopropylmethoxy)methyl)pyrrolidine-1-carboxylate

Product 1

HCID 568298573-((Cyclopropylmethoxy)methyl)pyrrolidineYield 65%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

tert-Butyl 3-[(cyclopropylmethoxy)methyl]pyrrolidine-1-carboxylate (Preparation 66, 50 g, 0.2 mol, 1 eq) was dissolved in isopropanol (200 mL) and treated with concentrated hydrogen chloride solution (28 mL, 0.3 mol, 1.5 eq). The mixture was refluxed for 1 h and evaporated. The residue was dissolved in water and washed with ether (2×100 mL). The aqueous fraction was made alkaline with potassium carbonate to pH 12-13 and extracted with chloroform. The extract was dried over sodium sulfate and evaporated to give title compound (20 g, 0.129 mol, 65%).

Workup

  1. temperatureThe mixture was refluxed for 1 h
  2. customevaporated
  3. dissolutionThe residue was dissolved in water
  4. washwashed with ether (2×100 mL)
  5. extractionextracted with chloroform
  6. dry with materialThe extract was dried over sodium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-f329980e9a6a43b09c136697426b9f9f
Source dataset
uspto-grants-2014_06
Patent number
US08741934B2

Reaction notes

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