Allyl iodide → HCID 66862712, compound

HRID 252998Notes

Reaction equation

HRID 252998 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]([N:12]2[CH2:16][CH2:15][CH2:14][C@H:13]2[CH2:17][OH:18])=[O:11])=[CH:6][CH:5]=1.[CH2:19](I)[CH:20]=[CH2:21].C(=O)([O-])O.[Na+]>CN(C)C=O>[CH2:21]([O:18][CH2:17][C@@H:13]1[CH2:14][CH2:15][CH2:16][N:12]1[C:10]([C:7]1[CH:8]=[CH:9][C:4]([Br:3])=[CH:5][CH:6]=1)=[O:11])[CH:20]=[CH2:19]

Participants

6

Reactant 4

HCID 11166Allyl iodideHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 28345615HCID 28345615, compound

Product 1

HCID 66862712HCID 66862712, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (61.5 mg, 1.41 mmol) (55% in paraffin liquid) was added to a solution of 200 mg (0.704 mmol) of (S)-(4-bromophenyl)(2-(hydroxymethyl)pyrrolidin-1-yl)methanone in N,N-dimethylformamide (2 ml) synthesized in the same manner as in step (i) of Reference Example 8, and the mixture was stirred at room temperature for 30 min. Thereafter, allyl iodide was added thereto, and the mixture was stirred at room temperature for 1 hr. The reaction was stopped by adding a saturated aqueous sodium hydrogencarbonate solution, and the reaction solution was extracted with ethyl acetate. The organic layer was washed with water and saturated brine in that order, was dried over anhydrous sodium sulfate, and was then filtered. The filtrate was concentrated under the reduced pressure, and the residue was purified by column chromatography on silica gel (hexane:ethyl acetate=1:2) to give 155 mg (yield 68%) of the title compound.

Workup

  1. customsynthesized in the same manner as in step (i) of Reference Example 8
  2. stirringthe mixture was stirred at room temperature for 1 hr
  3. extractionthe reaction solution was extracted with ethyl acetate
  4. washThe organic layer was washed with water and saturated brine in that order
  5. dry with materialwas dried over anhydrous sodium sulfate
  6. filtrationwas then filtered
  7. concentrationThe filtrate was concentrated under the reduced pressure
  8. customthe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=1:2)

Sources & evidence

ORD record
ord-69f1809a3ded4e379e5145d262ebb2ea
Source dataset
uspto-grants-2011_01
Patent number
US07871982B2

Reaction notes

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