Tetrahydro-4H-pyran-4-one → HCID 57635037, compound

HRID 2111249Notes

Reaction equation

HRID 2111249 reaction equation
FC(F)(F)C(O)=O.[CH2:8]([O:10][C:11](=[O:16])[CH:12]([CH3:15])[CH2:13][NH2:14])[CH3:9].[O:17]1[CH2:22][CH2:21][C:20](=O)[CH2:19][CH2:18]1.C([O-])(=O)C.[Na+].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>ClCCl>[CH2:8]([O:10][C:11](=[O:16])[CH:12]([CH3:15])[CH2:13][NH:14][CH:20]1[CH2:21][CH2:22][O:17][CH2:18][CH2:19]1)[CH3:9]

Participants

7

Reactant 5

HCID 121599Tetrahydro-4H-pyran-4-oneHCID 516892Sodium BicarbonateHCID 517045Sodium AcetateHCID 5049666Sodium triacetoxyborohydrideHCID 85718096HCID 85718096, compound

Product 1

HCID 57635037HCID 57635037, compoundYield 47.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4.904 g (0.020 mole) of (rac)-3-amino-2-methyl-propanoic acid ethyl ester trifluoroacetate in 100 mL of dichloromethane was added 2.0 g (0.02 mole) of tetrahydro-4H-pyran-4-one, 3.28 g (0.040 mole) of sodium acetate and 6.70 g (0.030 mole) of sodium triacetoxyborohydride. The mixture was stirred at room temperature for 16 hours and then 100 mL of saturated aqueous sodium bicarbonate solution (100 mL) was added. After stirring for another 30 minutes, the layers were separated. The aqueous layer was extracted twice with 100 mL of dichloromethane. The organic layers were washed with 100 mL of brine, combined, dried over anhydrous magnesium sulfate, filtered, and concentrated. The residue was distilled under vacuum to give 2.05 g of (rac)-2-methyl-3-(tetrahydro-pyran-4-ylamino)-propanoic acid ethyl ester as colorless oil. b.p. 135° C., 8 mm Hg.

Workup

  1. stirringAfter stirring for another 30 minutes
  2. customthe layers were separated
  3. extractionThe aqueous layer was extracted twice with 100 mL of dichloromethane
  4. washThe organic layers were washed with 100 mL of brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. distillationThe residue was distilled under vacuum

Sources & evidence

ORD record
ord-52d22d1523314421b54fb5f0bfa9eecd
Source dataset
uspto-grants-2009_04
Patent number
US07517873B2

Reaction notes

Loading…