1-tert-Butyl 2-methyl 2-{2-[(2-chlorophenyl)amino]ethyl}pyrrolidine-1,2-dicarboxylate → Tert-butyl 7-(2-chlorophenyl)-6-oxo-1,7-diazaspiro[4.4]nonane-1-carboxylate

HRID 1672376Notes

Reaction equation

HRID 1672376 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][CH2:9][CH2:10][C:11]1([C:23]([O:25]C)=O)[CH2:15][CH2:14][CH2:13][N:12]1[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17].C([Mg]Cl)(C)C>C1COCC1.CCOC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH2:9][CH2:10][C:11]2([N:12]([C:16]([O:18][C:19]([CH3:21])([CH3:20])[CH3:22])=[O:17])[CH2:13][CH2:14][CH2:15]2)[C:23]1=[O:25]

Participants

5

Reactant 2

HCID 673556421-tert-Butyl 2-methyl 2-{2-[(2-chlorophenyl)amino]ethyl}pyrrolidine-1,2-dicarboxylateHCID 178418918HCID 178418918, compound

Product 1

HCID 58948328Tert-butyl 7-(2-chlorophenyl)-6-oxo-1,7-diazaspiro[4.4]nonane-1-carboxylate

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

1-tert-Butyl 2-methyl 2-{2-[(2-chlorophenyl)amino]ethyl}pyrrolidine-1,2-dicarboxylate, was dissolved in anhydrous THF (4 mL) and cooled to 0° C. To this cooled solution was added isopropylmagnesium chloride in THF (2.0 M, 2 mL). The reaction vial was then sealed and heated to 64° C. and stirred for 18 h. The reaction mixture was then diluted with EtOAc and quenched by the addition of water. The crude mixture was filtered through a pad of diatomaceous earth and the filter pad was washed several times with EtOAc. The organic and aqueous layers of the filtrate were separated. The aqueous phase was extracted with EtOAc (3×10 mL) and the combined organic phases were washed with brine (2×5 mL), then dried (NaSO4), filtered, and concentrated in vacuo to afford the desired product. LC-MS: 251.1 (M−Boc+2H)+ and 295.1 (M−t-Bu+2H)+.

Workup

  1. customThe reaction vial was then sealed
  2. temperatureheated to 64° C.
  3. customquenched by the addition of water
  4. filtrationThe crude mixture was filtered through a pad of diatomaceous earth
  5. washthe filter pad was washed several times with EtOAc
  6. customThe organic and aqueous layers of the filtrate were separated
  7. extractionThe aqueous phase was extracted with EtOAc (3×10 mL)
  8. washthe combined organic phases were washed with brine (2×5 mL)
  9. dry with materialdried (NaSO4)
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-459c720572cc4e5f9720c8d721d1861c
Source dataset
uspto-grants-2011_08
Patent number
US07998959B2

Reaction notes

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