Ammonia → HCID 86691235, compound

HRID 2038219Notes

Reaction equation

HRID 2038219 reaction equation
[F:1][C:2]1[CH:14]=[CH:13][C:5]([O:6][CH2:7][C:8](=O)[CH2:9][O:10][CH3:11])=[CH:4][CH:3]=1.[BH4-].[Na+].[NH3:17]>>[F:1][C:2]1[CH:14]=[CH:13][C:5]([O:6][CH2:7][CH:8]([NH2:17])[CH2:9][O:10][CH3:11])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 4311764Sodium borohydrideHCID 86691233HCID 86691233, compound

Product 1

HCID 86691235HCID 86691235, compoundYield 78.6%

Procedure

Dissolve 1-(4-fluorophenoxy)-3-methoxy-propan-2-one (860 mg) in ammonia (7N in MeOH, 14.5 mL) and add molecular sieves (1 g). Stir the mixture at ambient temperature overnight. Cool the reaction to 0° C.; add sodium tetrahydroborate (0.66 g, 17.36 mmol); and stir the mixture at ambient temperature for 2 hours. Filter the mixture through a Celite® plug and rinse with MeOH. Concentrate the collected filtrate; dissolve in DCM; and wash with saturated aqueous NaHCO3 solution. Concentrate the filtrate under reduced pressure. Purify the mixture via SCX column, eluting with 7N NH3/MeOH to give the title compound (680 mg, 78.6%). MS (m/z): 200 (M+1).

Workup

  1. additionadd molecular sieves (1 g)
  2. temperatureCool
  3. customthe reaction to 0° C.
  4. stirringand stir the mixture at ambient temperature for 2 hours
  5. filtrationFilter the mixture through a Celite® plug
  6. washrinse with MeOH
  7. concentrationConcentrate the collected filtrate
  8. dissolutiondissolve in DCM
  9. washand wash with saturated aqueous NaHCO3 solution
  10. concentrationConcentrate the filtrate under reduced pressure
  11. customPurify the mixture via SCX column
  12. washeluting with 7N NH3/MeOH

Sources & evidence

ORD record
ord-9519adba6b2b4280895a09683eef46d0
Source dataset
uspto-grants-2013_11
Patent number
US08575352B2

Reaction notes

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