Acetic Acid → 5-Fluoro-6-[(tetrahydro-4H-pyran-3-yl)propylamino]benzoxazolin-2-one

HRID 1533875Notes

Reaction equation

HRID 1533875 reaction equation
[NH2:1][C:2]1[C:11]([F:12])=[CH:10][C:5]2[NH:6][C:7](=[O:9])[O:8][C:4]=2[CH:3]=1.[O:13]1[CH2:18][CH2:17][CH2:16][CH:15]([CH2:19][CH2:20][CH:21]=O)[CH2:14]1.C(O)(=O)C.C([BH3-])#N.[Na+]>CO>[F:12][C:11]1[C:2]([NH:1][CH2:21][CH2:20][CH2:19][CH:15]2[CH2:16][CH2:17][CH2:18][O:13][CH2:14]2)=[CH:3][C:4]2[O:8][C:7](=[O:9])[NH:6][C:5]=2[CH:10]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5003444Sodium cyanoborohydrideHCID 156759596-Amino-5-fluoro-2,3-dihydro-1,3-benzoxazol-2-oneHCID 15676001Tetrahydro-2H-pyran-3-propanal

Product 1

HCID 678348985-Fluoro-6-[(tetrahydro-4H-pyran-3-yl)propylamino]benzoxazolin-2-oneYield 38.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 6-amino-5-fluoro-benzoxazolin-2-one (2.1 g, 12.5 mmole) in methanol (80 ml) were added 3-(tetrahydro-2H-pyran-3-yl) propanal (1.95 g, 13.7 mmole) and acetic acid (1 ml) at room temperature, and then the mixture was stirred for 1 hour. Sodium cyanoborohydride (0.867 g, 13.7 mmole) was combined and stirring continued for 17 hours at room temperature. The reaction mixture was concentrated in vacuo, and the residue was treated with aqueous ammonium chloride solution. The organic substance was extracted with ethyl acetate/tetrahydrofuran. The extracts were washed with brine, dried over magnesium sulfate, and concentrated to afford crude product. This crude product was recrystallized from methanol to give 1.40 g of the title compound: m.p. 144°-145° C.

Workup

  1. stirringstirring
  2. waitcontinued for 17 hours at room temperature
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. additionthe residue was treated with aqueous ammonium chloride solution
  5. extractionThe organic substance was extracted with ethyl acetate/tetrahydrofuran
  6. washThe extracts were washed with brine
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated
  9. customto afford crude product
  10. customThis crude product was recrystallized from methanol

Sources & evidence

ORD record
ord-70c0d0afe04049e9bd90abb0d2b8e60c
Source dataset
uspto-grants-1992_02
Patent number
US05086062

Reaction notes

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