Hydrochloric Acid → HCID 18667537, compound

HRID 1059894Notes

Reaction equation

HRID 1059894 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([N:8]2[CH2:12][CH2:11][CH:10]([NH:13]C(OC(C)(C)C)=O)[CH2:9]2)[CH:3]=1.Cl>ClCCl.O1CCOCC1>[NH2:13][CH:10]1[CH2:11][CH2:12][N:8]([C:4]2[CH:3]=[C:2]([CH3:1])[CH:7]=[CH:6][N:5]=2)[CH2:9]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 18667607Tert-butyl (1-(4-methylpyridin-2-yl)pyrrolidin-3-yl)carbamate

Product 1

HCID 18667537HCID 18667537, compoundYield 88.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 1-(4-methylpyridin-2-yl)-3-(tert-butoxycarbonylamino)pyrrolidine (0.72 g) in dichloromethane (5 ml) was added a solution of hydrogen chloride in 1,4-dioxane (5 ml), and the resultant mixture was stirred at ambient temperature for 3 hours and evaporated under reduced pressure. To the residue was added 1N aqueous sodium hydroxide (30 ml) and extracted with ethyl acetate-tetrahydrofuran (2:1) three times. The combined organic layer was washed with brine, dried over sodium sulfate and evaporated under reduced pressure to give 3-amino-1-(4-methylpyridin-2-yl)pyrrolidine (409 mg).

Workup

  1. customevaporated under reduced pressure
  2. additionTo the residue was added 1N aqueous sodium hydroxide (30 ml)
  3. extractionextracted with ethyl acetate-tetrahydrofuran (2:1) three times
  4. washThe combined organic layer was washed with brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-33cc22f655ee4c8e88bf2033cfe7cfbc
Source dataset
uspto-grants-2003_02
Patent number
US06521643B1

Reaction notes

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