Sodium Hydroxide → HCID 18779184, compound

HRID 1422359Notes

Reaction equation

HRID 1422359 reaction equation
CO[N:3]=[CH:4][C:5]1[CH:6]=[C:7]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:8]=[CH:9][C:10]=1[CH2:11][OH:12].B.C1COCC1.[OH-].[Na+]>C1COCC1.O>[NH2:3][CH2:4][C:5]1[CH:6]=[C:7]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:8]=[CH:9][C:10]=1[CH2:11][OH:12]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 2723981Borane;tetrahydrofuranHCID 54497110HCID 54497110, compound

Product 1

HCID 18779184HCID 18779184, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the oxime from step B (0.51 g, 2.1 mmol) in THF (15 mL) at 0° C. was added BH3.THF (1M in hexane; 8 mL, 8 mmol) and the resulting solution was stirred at room temperature for 16 h then heated to reflux for 24 h. The solution was cooled to 0° C. and 1N NaOH (10 mL) was added slowly. After 1 h, the mixture was diluted with water, extracted with EtOAc (3×), washed with brine, dried and evaporated to give the title compound as an oil. This was used as such in the next step.

Workup

  1. temperaturethen heated
  2. temperatureto reflux for 24 h
  3. temperatureThe solution was cooled to 0° C.
  4. waitAfter 1 h
  5. extractionextracted with EtOAc (3×)
  6. washwashed with brine
  7. customdried
  8. customevaporated

Sources & evidence

ORD record
ord-e88f9ac12f2643919fada1d575eef7d6
Source dataset
uspto-grants-2000_06
Patent number
US06080870

Reaction notes

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