Trifluoroacetic acid → 1,1-Bis(phenylmethyl)-hexahydro-3H-oxazolo[3,4-a]pyrazin-3-one

HRID 1713490Notes

Reaction equation

HRID 1713490 reaction equation
[C:1]1([CH2:7][C:8]2([CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH:12]3[CH2:13][N:14](C(OC(C)(C)C)=O)[CH2:15][CH2:16][N:11]3[C:10](=[O:24])[O:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.FC(F)(F)C(O)=O>ClCCl>[C:26]1([CH2:25][C:8]2([CH2:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH:12]3[CH2:13][NH:14][CH2:15][CH2:16][N:11]3[C:10](=[O:24])[O:9]2)[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 231218621,1-dimethylethyl 1,1-bis(phenylmethyl)-tetrahydro-3-oxo-3H-oxazolo[3,4-a]pyrazine-7(1H)-carboxylate

Product 1

HCID 231219731,1-Bis(phenylmethyl)-hexahydro-3H-oxazolo[3,4-a]pyrazin-3-oneYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1,1-dimethylethyl 1,1-bis(phenylmethyl)-tetrahydro-3-oxo-3H-oxazolo[3,4-a]pyrazine-7(1H)-carboxylate (1.3 g, 3.2 mmol) in dichloromethane (15 mL) was added trifluoroacetic acid (4 mL), and the mixture was stirred at room temperature for 4 hours. The reaction solution was concentrated and extracted with ethyl acetate. The extract was washed with a 0.5 M aqueous sodium hydrogen carbonate solution, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. To the residue was added diethyl ether, the resulting crystals were collected by filtration and washed with diethyl ether to obtain the title compound (0.86 g, yield 85%).

Workup

  1. concentrationThe reaction solution was concentrated
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with a 0.5 M aqueous sodium hydrogen carbonate solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. additionTo the residue was added diethyl ether
  7. filtrationthe resulting crystals were collected by filtration
  8. washwashed with diethyl ether

Sources & evidence

ORD record
ord-0481b4f0a1554584bf4f9f3aecc9ff91
Source dataset
uspto-grants-2010_09
Patent number
US07795267B2

Reaction notes

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