Potassium Iodide → HCID 67523962, compound

HRID 1170399Notes

Reaction equation

HRID 1170399 reaction equation
Cl[CH2:2][CH2:3][CH2:4][C:5](Cl)=[O:6].Cl.[NH2:9][CH:10]([C:23]1[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=1)[CH:11]([C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][CH:14]=1)[OH:12].C(N(CC)CC)C.[OH-].[Na+].[I-].[K+].P([O-])(O)(O)=O.[Na+]>CN(C=O)C>[F:29][C:26]1[CH:25]=[CH:24][C:23]([CH:10]([N:9]2[CH2:2][CH2:3][CH2:4][C:5]2=[O:6])[CH:11]([OH:12])[C:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=[CH:15][CH:14]=2)=[CH:28][CH:27]=1

Participants

8

Reactant 6

HCID 4875Potassium IodideHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 783704-Chlorobutyryl chlorideHCID 23672064Monosodium phosphateHCID 67523989HCID 67523989, compound

Product 1

HCID 67523962HCID 67523962, compoundYield 12%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
-10 °C

Procedure

2.15 ml (18.1 mmol) of 4-chlorobutyryl chloride (95%) were slowly added dropwise to a solution of 5.5 g (17.3 mmol) of 2-amino-2-(4-fluorophenyl)-1-naphthalen-1-ylethanol hydrochloride and 7.2 ml (51.7 mmol) of triethylamine in 55 ml of DMF cooled to −10° C. After stirring at room temperature for 2.5 h, 8.3 g (208 mmol) of sodium hydroxide pellets and 862 mg (5.2 mmol) of potassium iodide were added, and the mixture was stirred at room temperature overnight. The mixture was poured into an aqueous sodium dihydrogen phosphate solution (80 g/l). Extraction twice with diisopropyl ether was followed by drying over magnesium sulfate. The residue after concentration in vacuo was purified by chromatography with petroleum benzene/ethyl acetate 50:50. 3.8 g of 1-[1-(4-fluorophenyl)-2-hydroxy-2-naphthalen-1-ylethyl]pyrrolidin-2-one (diastereoisomer A) (yield: 63%) and 728 mg of 1-[1-(4-fluorophenyl)-2-hydroxy-2-(1-naphthyl)ethyl]pyrrolidin-2-one (diastereomer B) (yield: 12%) were obtained.

Workup

  1. stirringthe mixture was stirred at room temperature overnight
  2. extractionExtraction twice with diisopropyl ether
  3. dry with materialby drying over magnesium sulfate
  4. concentrationThe residue after concentration in vacuo
  5. customwas purified by chromatography with petroleum benzene/ethyl acetate 50:50

Sources & evidence

ORD record
ord-b8ca716091dd4b8886a5d198c3d20e29
Source dataset
uspto-grants-2010_11
Patent number
US07825264B2

Reaction notes

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