Trifluoroacetic acid → 1,1-Diphenyltetrahydro-1H-oxazolo[3,4-a]pyrazin-3(5H)-one

HRID 1713479Notes

Reaction equation

HRID 1713479 reaction equation
CC(OC([N:8]1[CH2:13][CH2:12][N:11]2[C:14](=[O:29])[O:15][C:16]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:10]2[CH2:9]1)=O)(C)C.FC(F)(F)C(O)=O.C(=O)([O-])O.[Na+]>ClCCl>[C:23]1([C:16]2([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:10]3[CH2:9][NH:8][CH2:13][CH2:12][N:11]3[C:14](=[O:29])[O:15]2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 68420957(1,1-dimethylethyl)tetrahydro-3-oxo-1,1-diphenyl-3H-oxazolo[3,4-a]pyrazine-7(1H)-carboxylate

Product 1

HCID 231218811,1-Diphenyltetrahydro-1H-oxazolo[3,4-a]pyrazin-3(5H)-oneYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (1,1-dimethylethyl)tetrahydro-3-oxo-1,1-diphenyl-3H-oxazolo[3,4-a]pyrazine-7(1H)-carboxylate (2.3 g, 5.5 mmol) in dichloromethane (20 mL) was added trifluoroacetic acid (4 mL), and the mixture was stirred at room temperature for 2 hours. To the reaction solution was added an aqueous saturated sodium hydrogen carbonate solution (10 mL), and the resulting mixture was extracted with ethyl acetate. The extract was washed with water, and then concentrated under reduced pressure. The residue was crystallized from diisopropyl ether to obtain the title compound (1.6 g, yield 99%).

Workup

  1. extractionthe resulting mixture was extracted with ethyl acetate
  2. washThe extract was washed with water
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was crystallized from diisopropyl ether

Sources & evidence

ORD record
ord-cf9ca9f458644555aa8bf3187672cae4
Source dataset
uspto-grants-2010_09
Patent number
US07795267B2

Reaction notes

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