Acetone → HCID 19882669, compound

HRID 653750Notes

Reaction equation

HRID 653750 reaction equation
[ClH:1].[F:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]([CH2:13][NH2:14])[CH2:8][CH2:7][CH2:6]2.[CH3:15][C:16]([CH3:18])=O.C([BH3-])#N.[Na+]>CO>[ClH:1].[CH:16]([NH:14][CH2:13][CH:9]1[C:10]2[C:5](=[CH:4][C:3]([F:2])=[CH:12][CH:11]=2)[CH2:6][CH2:7][CH2:8]1)([CH3:18])[CH3:15]

Participants

5

Reactant 3

HCID 180AcetoneHCID 5003444Sodium cyanoborohydride2×HCID 19882627HCID 19882627, compound

Product 1

HCID 19882669HCID 19882669, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The product from Example 75 (1.5 g) was added to a solution of acetone (25 ml) and MeOH (25 ml) then 95% sodium cyanoborohydride (1.32 g) was added in portions. The pH of the reaction was adjusted to ca. pH 5 after complete addition of the NaBH3CN. The reaction was then stirred at room temperature for 8 hrs. The reaction was evaporated to dryness, then dilute HCl and CH2Cl2 (50 ml) was added. The aqueous layer was separated, basified then CH2Cl2 added. The organic layer was separated, dried (MgSO4), filtered and evaporated. The residue was taken up in Et2O (300 ml) then ethereal HCl added. The resulting precipitate was filtered and recrystallized from EtOAc/MeOH giving the desired compound, m.p. 212°-14° C.

Workup

  1. customThe reaction was evaporated to dryness
  2. additiondilute HCl and CH2Cl2 (50 ml) was added
  3. customThe aqueous layer was separated
  4. additionCH2Cl2 added
  5. customThe organic layer was separated
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customevaporated
  9. additionethereal HCl added
  10. filtrationThe resulting precipitate was filtered
  11. customrecrystallized from EtOAc/MeOH giving the desired compound, m.p. 212°-14° C.

Sources & evidence

ORD record
ord-8e3ea061cd1b4e0e817cb4b7d5fd54ff
Source dataset
uspto-grants-1992_07
Patent number
US05128362

Reaction notes

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