Triethylamine → HCID 57988768, compound

HRID 889044Notes

Reaction equation

HRID 889044 reaction equation
[O:1]=[C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([F:16])([F:15])[F:14])[CH:8]=2)[CH2:5][CH:4]([C:17]([OH:19])=O)[CH2:3]1.C(N1C=CN=C1)(N1C=CN=C1)=O.Cl.[CH3:33][NH:34][O:35][CH3:36].C(N(CC)CC)C>C(Cl)Cl.O>[CH3:36][O:35][N:34]([CH3:33])[C:17]([CH:4]1[CH2:3][C:2](=[O:1])[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([F:14])([F:15])[F:16])[CH:8]=2)[CH2:5]1)=[O:19]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 2775915HCID 2775915, compound

Product 1

HCID 57988768HCID 57988768, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of [5-oxo-1-(3-trifluoromethyl-phenyl)-pyrrolidine-3-carboxylic acid (1 g, 3.66 mmol) in DCM (15 mL) was added 1,1′-carbonyldiimidazole (0.65 g, 4.02 mmol) portion wise over a period of 10 min at 10-15° C. N,O-dimethylhydroxylamine hydrochloride (0.42 g, 4.39 mmol) was added portion wise and stirred for 5 min at that temperature. To the reaction mixture triethylamine (0.66 ml, 4.75 mmol) was added drop wise and it was stirred for 2 hr at 20-25° C. The reaction mixture was diluted with water (10 ml) and aqueous layer was separated. The aqueous layer was extracted with DCM (2×25 ml). The combined organic layer was washed with 5% HCl (25 ml) and saturated brine solution (25 ml). The organic layer was dried over Na2SO4, evaporated under reduced pressure to obtain 5-oxo-1-(3-trifluoromethyl-phenyl)-pyrrolidine-3-carboxylic acid methoxy-methyl-amide (0.95 g, 83%) as a colorless sticky mass.

Workup

  1. stirringit was stirred for 2 hr at 20-25° C
  2. customwas separated
  3. extractionThe aqueous layer was extracted with DCM (2×25 ml)
  4. washThe combined organic layer was washed with 5% HCl (25 ml) and saturated brine solution (25 ml)
  5. dry with materialThe organic layer was dried over Na2SO4
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-c4a688066cad438f8310d94fc6e79abc
Source dataset
uspto-grants-2012_08
Patent number
US08252797B2

Reaction notes

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