Lithium diisopropylamide → HCID 18430916, compound

HRID 1278624Notes

Reaction equation

HRID 1278624 reaction equation
C([N-]C(C)C)(C)C.[Li+].[CH2:9]([N:16]1[CH2:21][CH2:20][N:19]([CH2:22][CH2:23][CH:24]([CH2:30][CH2:31][CH2:32][CH2:33]I)[C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH2:18][CH2:17]1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>O1CCCC1>[CH2:9]([N:16]1[CH2:21][CH2:20][N:19]([CH2:22][CH2:23][C:24]2([C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH2:33][CH2:32][CH2:31][CH2:30]2)[CH2:18][CH2:17]1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 2724682Lithium diisopropylamideHCID 18430942HCID 18430942, compound

Product 1

HCID 18430916HCID 18430916, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a stirred solution of lithium diisopropylamide (2 M, 13.3 ml, 26.7 mmol) in tetrahydrofuran (113 ml) was added the solution of ethyl 2-[2-(4-benzyl-1-piperazinyl)ethyl]-6-iodohexanoate (6.3 g) in tetrahydrofuran (20 ml) at −78° C. After 30 min, the temperature was gradually raised to 0° C. during a period of 30 min. After 15 min at 0° C., the reaction was quenched by adding AcOH (0.230 ml). After the mixture was basified with aq. saturated NaHCO3, then the resulting mixture was extracted with ethyl acetate. The extract was washed with brine, dried over NASO4, filtered and concentrated in vacuo. The residue was purified by column chromatography (SiO2, 200-350 mesh/500 g/hexane:ethyl acetate=2:1) to provide a yellow oil (4.2 g/92%).

Workup

  1. waitAfter 15 min at 0° C.
  2. customthe reaction was quenched
  3. additionby adding AcOH (0.230 ml)
  4. extractionthe resulting mixture was extracted with ethyl acetate
  5. washThe extract was washed with brine
  6. customdried over NASO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by column chromatography (SiO2, 200-350 mesh/500 g/hexane:ethyl acetate=2:1)
  10. customto provide a yellow oil (4.2 g/92%)

Sources & evidence

ORD record
ord-f35b8ff9f2e741d4858c7c671934c925
Source dataset
uspto-grants-2002_09
Patent number
US06444677B2

Reaction notes

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