Trifluoroacetic acid → Rac-2-methyl-3-phenyl-2,6-diazaspiro[3.5]nonan-1-one

HRID 1036733Notes

Reaction equation

HRID 1036733 reaction equation
[CH3:1][N:2]1[CH:5]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:4]2([CH2:16][CH2:15][CH2:14][N:13](C(OC(C)(C)C)=O)[CH2:12]2)[C:3]1=[O:24].C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:1][N:2]1[CH:5]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:4]2([CH2:16][CH2:15][CH2:14][NH:13][CH2:12]2)[C:3]1=[O:24]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 71060344Tert-butyl 2-methyl-1-oxo-3-phenyl-2,6-diazaspiro[3.5]nonane-6-carboxylate

Product 1

HCID 71060408Rac-2-methyl-3-phenyl-2,6-diazaspiro[3.5]nonan-1-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution comprising tert-butyl 2-methyl-1-oxo-3-phenyl-2,6-diazaspiro[3.5]nonane-6-carboxylate (1.2 g, 3.63 mmol) and TFA (1.399 ml, 18.16 mmol) in DCM (20 ml) was stirred at RT for 4 days. The reaction mixture was concentrated in vacuo and the resulting crude product was dissolved with methanol (5 ml) and passed through a 10 g SCX-2 cartridge. The product was eluted with 2M NH3 in methanol (70 ml) and the relevant fractions were combined and concentrated in vacuo to afford the title compound as a yellow oil;

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutionthe resulting crude product was dissolved with methanol (5 ml)
  3. washThe product was eluted with 2M NH3 in methanol (70 ml)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3de07fc0f22948709b9bab385a90bcb4
Source dataset
uspto-grants-2013_10
Patent number
US08546416B2

Reaction notes

Loading…