Triethylamine → HCID 58646897, compound

HRID 1244861Notes

Reaction equation

HRID 1244861 reaction equation
[CH:1]1([CH2:5][NH:6][C@H:7]2[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8]2)[CH2:4][CH2:3][CH2:2]1.[F:19][C:20]([F:31])([F:30])[C:21]1[CH:29]=[CH:28][CH:27]=[CH:26][C:22]=1[C:23](Cl)=[O:24].C(N(CC)CC)C>C1(C)C=CC=CC=1>[CH:1]1([CH2:5][N:6]([C:23](=[O:24])[C:22]2[CH:26]=[CH:27][CH:28]=[CH:29][C:21]=2[C:20]([F:19])([F:30])[F:31])[C@H:7]2[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8]2)[CH2:2][CH2:3][CH2:4]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 675612-(Trifluoromethyl)benzoyl chlorideHCID 58718604HCID 58718604, compound

Product 1

HCID 58646897HCID 58646897, compoundYield 104.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

tert-butyl (3S)-3-[(cyclobutylmethyl)amino]pyrrolidine-1-carboxylate (0.80 g, 3.15 mmol) in toluene (10 ml) was treated with 2-(trifluoromethyl)benzoyl chloride (0.55 ml, 3.78 mmol) and triethylamine (0.88 ml, 6.3 mmol). The solution was stirred for 18 hours at room temperature and the solvent removed under reduced pressure. The crude product was purified by column chromatography on silica gel using a gradient of pentane:ethylacetate (4:1 by volume) changing to pentane:ethylacetate (1:1 by volume) to afford the title compound as a colorless oil (1.40 g, crude) which is used directly in the next step.

Workup

  1. customthe solvent removed under reduced pressure
  2. customThe crude product was purified by column chromatography on silica gel using a gradient of pentane:ethylacetate (4:1 by volume)

Sources & evidence

ORD record
ord-8951af09e41e42898d952ded74ed2389
Source dataset
uspto-grants-2006_10
Patent number
US07122683B2

Reaction notes

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