Trifluoroacetic acid → (9aR)-Hexahydropyrazino[2,1-c][1,4]oxazin-4(3H)-one

HRID 2066531Notes

Reaction equation

HRID 2066531 reaction equation
C(OC([N:8]1[CH2:17][CH2:16][N:15]2[C@@H:10]([CH2:11][O:12][CH2:13][C:14]2=[O:18])[CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:11]1[C@H:10]2[CH2:9][NH:8][CH2:17][CH2:16][N:15]2[C:14](=[O:18])[CH2:13][O:12]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58117095HCID 58117095, compound

Product 1

HCID 16124470(9aR)-Hexahydropyrazino[2,1-c][1,4]oxazin-4(3H)-oneYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (R)-4-oxo-hexahydro-pyrazino[2,1-c][1,4]oxazine-8-carboxylic acid tert-butyl ester in DCM (5 mL) was added TFA (1 mL). The resulting mixture was stirred at RT for 2 h then concentrated in vacuo. The resulting residue was azeotroped with toluene then purified by SCX column to give the title compound as a colourless oil (60 mg, 76%).

Workup

  1. concentrationthen concentrated in vacuo
  2. customThe resulting residue was azeotroped with toluene
  3. customthen purified by SCX column

Sources & evidence

ORD record
ord-982ec4c61c4247c188d73c7fc6dbefaf
Source dataset
uspto-grants-2012_10
Patent number
US08293735B2

Reaction notes

Loading…