Hydrochloric Acid → (3-Cyclopropyl-1,2-oxazol-5-yl)methanamine

HRID 2105223Notes

Reaction equation

HRID 2105223 reaction equation
C(OC([NH:8][CH2:9][C:10]1[O:14][N:13]=[C:12]([CH:15]2[CH2:17][CH2:16]2)[CH:11]=1)=O)(C)(C)C.Cl>CO>[NH2:8][CH2:9][C:10]1[O:14][N:13]=[C:12]([CH:15]2[CH2:17][CH2:16]2)[CH:11]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 688156195-(tert-Butoxycarbonylaminomethyl)-3-cyclopropylisoxazole

Product 1

HCID 64156762(3-Cyclopropyl-1,2-oxazol-5-yl)methanamineYield 53%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Crude 5-(tert-butoxycarbonylaminomethyl)-3-cyclopropylisoxazole (Method 3) (37.4 g, 0.157 mol) and 3M hydrochloric acid (80 ml) in methanol (100 ml) was heated at 50° C. for 2 hours. The methanol was removed by evaporation and aqueous residue washed with DCM. The aqueous layer was adjusted to pH 12 by careful addition of 40% aqueous sodium hydroxide solution and then extracted with DCM (×4). The extracts were combined, washed with brine, then dried (Na2SO4) and the volatiles removed by evaporation to give the title compound (11.5 g, 53%) as oil.

Workup

  1. customThe methanol was removed by evaporation and aqueous residue
  2. washwashed with DCM
  3. additionThe aqueous layer was adjusted to pH 12 by careful addition of 40% aqueous sodium hydroxide solution
  4. extractionextracted with DCM (×4)
  5. washwashed with brine
  6. dry with materialdried (Na2SO4)
  7. customthe volatiles removed by evaporation

Sources & evidence

ORD record
ord-c818c0c7bd1c4ffab309d7af90a8cc5b
Source dataset
uspto-grants-2009_08
Patent number
US07579349B2

Reaction notes

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