Triethylamine → (S)-1-(2-Bromo-acetyl)-pyrrolidine-2-carboxylic acid cyclopropylamide

HRID 1185428Notes

Reaction equation

HRID 1185428 reaction equation
[Br:1][CH2:2][C:3](Br)=[O:4].Cl.[CH:7]1([NH:10][C:11]([C@@H:13]2[CH2:17][CH2:16][CH2:15][NH:14]2)=[O:12])[CH2:9][CH2:8]1.C(N(CC)CC)C>C(Cl)Cl.CN(C1C=CN=CC=1)C.C(OCC)(=O)C>[CH:7]1([NH:10][C:11]([C@@H:13]2[CH2:17][CH2:16][CH2:15][N:14]2[C:3](=[O:4])[CH2:2][Br:1])=[O:12])[CH2:9][CH2:8]1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 61147Bromoacetyl bromideHCID 66855012(S)-N-cyclopropylpyrrolidine-2-carboxamide hydrochloride

Product 1

HCID 68600753(S)-1-(2-Bromo-acetyl)-pyrrolidine-2-carboxylic acid cyclopropylamide

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1.2 g of bromo-acetyl bromide in 30 ml of DCM a solution of 1 g of (S)-Pyrrolidine-2-carboxylic acid cyclopropylamide hydrochloride, 0.6 g of triethylamine and 7 mg of DMAP in 10 ml of DCM was added drop-wise at 0° C. After 1 h the reaction mixture was diluted with ethyl acetate and the solids were filtered off. The organic phase was evaporated under reduced pressure and the residue was filtered over silica gel eluting with ethyl acetate/heptane (8/2). After evaporation of the solvent the obtained product was pure enough for the subsequent reaction step. Yield: 1.3 g.

Workup

  1. filtrationthe solids were filtered off
  2. customThe organic phase was evaporated under reduced pressure
  3. filtrationthe residue was filtered over silica gel eluting with ethyl acetate/heptane (8/2)
  4. customAfter evaporation of the solvent the obtained product
  5. customwas pure enough for the subsequent reaction step

Sources & evidence

ORD record
ord-2798415fcf58488d94236db9eeabf200
Source dataset
uspto-grants-2014_03
Patent number
US08669266B2

Reaction notes

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