2-Chloroaniline → 1-tert-Butyl 2-methyl 2-{2-[(2-chlorophenyl)amino]ethyl}pyrrolidine-1,2-dicarboxylate

HRID 1672375Notes

Reaction equation

HRID 1672375 reaction equation
O=[CH:2][CH2:3][C:4]1([C:16]([O:18][CH3:19])=[O:17])[CH2:8][CH2:7][CH2:6][N:5]1[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10].[Cl:20][C:21]1[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=1[NH2:23].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl.CCOC(C)=O>[Cl:20][C:21]1[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=1[NH:23][CH2:2][CH2:3][C:4]1([C:16]([O:18][CH3:19])=[O:17])[CH2:8][CH2:7][CH2:6][N:5]1[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10]

Participants

6

Reactant 3

HCID 72402-ChloroanilineHCID 5049666Sodium triacetoxyborohydrideHCID 738300911-Tert-butyl 2-methyl 2-(2-oxoethyl)pyrrolidine-1,2-dicarboxylate

Product 1

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

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1-tert-butyl 2-methyl 2-(2-oxoethyl)pyrrolidine-1,2-dicarboxylate (220 mg, 0.00081 mol) in DCM (anhydrous, 4 mL) was added to 2-chloroaniline (110 μL, 0.0010 mol) and the resulting solution was stirred for 20 min. Sodium triacetoxyborohydride (290 mg, 0.0014 mol) was then added to the mixture. After stirring at RT for 12 h, the reaction mixture was 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 were washed several times with EtOAc and the resulting layers were of the filtrate separated. The aqueous phase was extracted with EtOAc (3×10 mL) and the combined organic phases were washed with brine (2×5 mL). The organic phase was then dried (NaSO4), filtered, and concentrated in vacuo to afford the desired product. LC-MS: 327.1 (M−Boc+2H)+ and 383.2 (M+1H)+.

Workup

  1. stirringAfter stirring at RT for 12 h
  2. customquenched by the addition of water
  3. filtrationThe crude mixture was filtered through a pad of diatomaceous earth
  4. washthe filter pad were washed several times with EtOAc
  5. customseparated
  6. extractionThe aqueous phase was extracted with EtOAc (3×10 mL)
  7. washthe combined organic phases were washed with brine (2×5 mL)
  8. dry with materialThe organic phase was then dried (NaSO4)
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-99972d8793f24f0b80909011960b04e6
Source dataset
uspto-grants-2011_08
Patent number
US07998959B2

Reaction notes

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