Potassium Phosphate, Tribasic → HCID 64387590, compound

HRID 1911295Notes

Reaction equation

HRID 1911295 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH2:7])=[CH:4][CH:3]=1.[CH3:10][C:11]([CH:13]([O:16][CH3:17])[O:14][CH3:15])=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[O-]P([O-])([O-])=O.[K+].[K+].[K+]>ClCCCl>[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH:7][CH:11]([CH3:10])[CH:13]([O:16][CH3:17])[O:14][CH3:15])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 673264-FluorobenzylamineHCID 80650Pyruvic aldehyde dimethyl acetalHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 64387590HCID 64387590, compoundYield 98.1%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

4-Fluorobenzylamine (3.00 mL, 26.2 mmol), pyruvic aldehyde dimethyl acetal (3.11 mL, 26.2 mmol), DCE (87 mL), and sodium triacetoxyborohydride (7.79 g, 36.7 mmol) were stirred at ambient temperature. After 14 hours, the reaction was complete as indicated by LCMS. To the reaction mixture was added 30% aqueous K3PO4 (pH=14; 60 mL). The layers were partitioned and the aqueous layer was, extracted with EtOAc (2×50 mL), and washed with brine (60 mL). The organic portion was dried (Na2SO4), filtered, and concentrated to give the title compound (5.83 g, 25.7 mmol, 98% yield). MS (DCI/NH3) m/z 228 (M+H)+.

Workup

  1. customThe layers were partitioned
  2. extractionextracted with EtOAc (2×50 mL)
  3. washwashed with brine (60 mL)
  4. dry with materialThe organic portion was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-4f1fd2e571d7441a95e01fb136e1b74b
Source dataset
uspto-grants-2013_12
Patent number
US08604053B2

Reaction notes

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