Trifluoroacetic acid → HCID 71060192, compound

HRID 1036701Notes

Reaction equation

HRID 1036701 reaction equation
[CH3:1][N:2]1[CH2:17][CH:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:4]2([CH2:8][N:7](C(OC(C)(C)C)=O)[CH2:6][CH2:5]2)[C:3]1=[O:24].C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:1][N:2]1[CH2:17][CH:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:4]2([CH2:5][CH2:6][NH:7][CH2:8]2)[C:3]1=[O:24]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 71060643HCID 71060643, compound

Product 1

HCID 71060192HCID 71060192, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl 7-methyl-6-oxo-9-phenyl-2,7-diazaspiro[4.4]nonane-2-carboxylate (diastereomer 1, step 1) (488.3 mg, 1.48 mmol) in DCM (10 mL) was treated with TFA (2.3 mL, 29.6 mmol). The reaction mixture was stirred at room temperature for 5 hours and concentrated in vacuo. The residue was dissolved in EtOAc and washed with a saturated sodium bicarbonate solution. The organic portion was dried (MgSO4), filtered and concentrated in vacuo to afford the title compound which was used in the next step without further purification;

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in EtOAc
  3. washwashed with a saturated sodium bicarbonate solution
  4. dry with materialThe organic portion was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6f83124b42584019855cb953cb634471
Source dataset
uspto-grants-2013_10
Patent number
US08546416B2

Reaction notes

Loading…