Triethylamine → HCID 59540381, compound

HRID 923435Notes

Reaction equation

HRID 923435 reaction equation
Br[CH:2]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:3]([O:5][C@H:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH3:7])=[O:4].C(N(CC)CC)C.Cl.[F:28][C:29]1([F:35])[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1>O1CCCC1.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[F:28][C:29]1([F:35])[CH2:34][CH2:33][N:32]([CH:2]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:3]([O:5][C@H:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH3:7])=[O:4])[CH2:31][CH2:30]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 27583514,4-Difluoropiperidine hydrochlorideHCID 59166394(S)-1-Phenylethyl 2-bromo-2-phenylacetate

Product 1

HCID 59540381HCID 59540381, compoundYield 92.4%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
55 °C

Procedure

To a solution of the product from Example 138A (1.00 g, 3.13 mmol) in tetrahydrofuran (20 mL) at room temperature was added triethylamine (1.75 mL, 12.5 mmol) and tetrabutylammonium iodide (0.46 g, 1.25 mmol). The mixture was stirred for 5 minutes and then 4,4-difluoropiperidine hydrochloride (0.74 g, 4.70 mmol) was added as the free base in THF. The mixture was stirred for 1 hour at room temperature and then heated to 55° C. overnight. The cooled mixture was washed with brine, concentrated, then purified by column chromatography (EtOAc-hexane) to provide the title compound (1.04 g, 92% yield).

Workup

  1. stirringThe mixture was stirred for 1 hour at room temperature
  2. washThe cooled mixture was washed with brine
  3. concentrationconcentrated
  4. custompurified by column chromatography (EtOAc-hexane)

Sources & evidence

ORD record
ord-3b43cd5895394a27a705b7731ed47867
Source dataset
uspto-grants-2016_03
Patent number
US09278922B2

Reaction notes

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