Ammonium Acetate → HCID 59192499, compound

HRID 2384016Notes

Reaction equation

HRID 2384016 reaction equation
[C:1]([O:5][C:6](=[O:21])[CH2:7][O:8][C:9]1[C:18]2[CH2:17][CH2:16][CH2:15][CH2:14][C:13]=2[CH:12]=[C:11]([Cl:19])[C:10]=1[F:20])([CH3:4])([CH3:3])[CH3:2].C([O-])(=O)C.[NH4+].C([BH3-])#[N:28].[Na+]>CO>[C:1]([O:5][C:6](=[O:21])[CH2:7][O:8][C:9]1[C:18]2[CH2:17][CH2:16][CH2:15][CH:14]([NH2:28])[C:13]=2[CH:12]=[C:11]([Cl:19])[C:10]=1[F:20])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 68544738HCID 68544738, compound

Product 1

HCID 59192499HCID 59192499, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred and ice cold solution of (3-chloro-2-fluoro-5,6,7,8-tetrahydro-naphthalen-1-yloxy)-acetic acid tert-butyl ester (1.32 g, 4.01 mmol) and ammonium acetate (4.7 g, 61.0 mmol) in methanol (21 mL) was added sodium cyanoborohydride (504 mg, 8.02 mmol) under nitrogen. After 10 minutes of stirring at room temperature, the reaction mixture was heated at reflux for 4 hours. The solvent was removed under reduced pressure and to the residue was added saturated sodium bicarbonate solution (10 mL). The resulting solution was extracted with dichloromethane (25 mL×3). The organic layers were dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to afford (5-amino-3-chloro-2-fluoro-5,6,7,8-tetrahydro-naphthalen-1-yloxy)-acetic acid tert-butyl ester (1.26 g, 98%), which is used in the next step without further purification.

Workup

  1. stirringAfter 10 minutes of stirring at room temperature
  2. temperaturethe reaction mixture was heated
  3. temperatureat reflux for 4 hours
  4. customThe solvent was removed under reduced pressure and to the residue
  5. additionwas added saturated sodium bicarbonate solution (10 mL)
  6. extractionThe resulting solution was extracted with dichloromethane (25 mL×3)
  7. dry with materialThe organic layers were dried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2939deffcaec43d787cca1b148e5e42a
Source dataset
uspto-grants-2012_09
Patent number
US08263656B2

Reaction notes

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