Sodium hydride → HCID 69144021, compound

HRID 1794149Notes

Reaction equation

HRID 1794149 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:7]([I:10])=[CH:6][C:3]=1[CH2:4][OH:5].[C:11]([O:15][C:16]([N:18]1[CH2:23][CH2:22][N:21]([C:24](Cl)=[O:25])[C@H:20]([CH2:27][CH3:28])[CH2:19]1)=[O:17])([CH3:14])([CH3:13])[CH3:12].[H-].[Na+]>CN(C)C=O>[F:1][C:2]1[CH:9]=[CH:8][C:7]([I:10])=[CH:6][C:3]=1[CH2:4][O:5][C:24]([N:21]1[CH2:22][CH2:23][N:18]([C:16]([O:15][C:11]([CH3:13])([CH3:12])[CH3:14])=[O:17])[CH2:19][C@H:20]1[CH2:27][CH3:28])=[O:25]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 22220046HCID 22220046, compoundHCID 86586001(R)-4-Chlorocarbonyl-3-ethyl-piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 69144021HCID 69144021, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A mixture of 2-fluoro-5-iodo-benzylalcohol (5.0 g, 19.8 mM) and (R)-4-chlorocarbonyl-3-ethyl-piperazine-1-carboxylic acid tert-butyl ester (5.5 g, 19.8 mM) in dimethylformamide (70 mL) was added slowly to a suspension of sodium hydride (1.3 g, 55%, 1.89 mM) in dimethylformamide (30 mL). The mixture was stirred at room temperature for 5 h and partitioned between water and diethylether. Organic phases were pooled, washed with brine and dried with Na2SO4 to yield after evaporation a yellow oil (11.2 g). This residue was purified by column chromatography (silica gel; n-hexane/ethylacetate 3:1) to yield 9.4 g (97%) of the product as a yellowish oil. MS (ISP): 510.3 (M+NH4)+.

Workup

  1. custompartitioned between water and diethylether
  2. washwashed with brine
  3. dry with materialdried with Na2SO4
  4. customto yield
  5. customafter evaporation a yellow oil (11.2 g)
  6. customThis residue was purified by column chromatography (silica gel; n-hexane/ethylacetate 3:1)

Sources & evidence

ORD record
ord-7c696e5f1bb24e98958a2a121dbefcee
Source dataset
uspto-grants-2006_04
Patent number
US07022707B2

Reaction notes

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