Lithium diisopropylamide → HCID 178515503, compound

HRID 1672738Notes

Reaction equation

HRID 1672738 reaction equation
[F:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([N:8]2[CH2:12][CH2:11][CH2:10][C:9]2=[O:13])[CH2:4][CH2:3]1.[Li+].CC([N-]C(C)C)C.[Br:22][C:23]1[CH:28]=[CH:27][C:26]([CH2:29]Br)=[C:25]([Cl:31])[CH:24]=1>C1COCC1>[Br:22][C:23]1[CH:28]=[CH:27][C:26]([CH2:29][CH:10]2[CH2:11][CH2:12][N:8]([C@H:5]3[CH2:6][CH2:7][C@H:2]([F:1])[CH2:3][CH2:4]3)[C:9]2=[O:13])=[C:25]([Cl:31])[CH:24]=1

Participants

5

Reactant 3

HCID 2724682Lithium diisopropylamideHCID 219144864-Bromo-1-(bromomethyl)-2-chlorobenzeneHCID 178516222HCID 178516222, compound

Product 1

HCID 178515503HCID 178515503, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of trans-1-(4-fluoro-cyclohexyl)-pyrrolidin-2-one (Preparation 24) (20 mg, 0.11 mmol) in 3 mL dry THF, add 0.165 mL of 2M LDA (1.5 eq.) in THF dropwise at −78° C. Then, add 16 mg of 4-Bromo-1-bromomethyl-2-chloro-benzene (2 eq) at −78° C. Allow the resulting solution to stand at room temp for overnight. Quench the mixture with saturated aqueous NH4Cl and extract with CH2Cl2. Wash the organic layer with water, brine, dry over Na2SO4, filter and concentrate. Purify the crude material by chromatography to afford 10.5 mg of the title compound: mass spectrum (m/z): 389 (M+1).

Workup

  1. customQuench the mixture with saturated aqueous NH4Cl
  2. extractionextract with CH2Cl2
  3. washWash the organic layer with water, brine
  4. dry with materialdry over Na2SO4
  5. filtrationfilter
  6. concentrationconcentrate
  7. customPurify the crude material by chromatography

Sources & evidence

ORD record
ord-c808a7866a274c8db00df4e890ed6167
Source dataset
uspto-grants-2011_08
Patent number
US07998999B2

Reaction notes

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