Lithium diisopropylamide → HCID 178515502, compound

HRID 1672739Notes

Reaction equation

HRID 1672739 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 178516221HCID 178516221, compound

Product 1

HCID 178515502HCID 178515502, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of cis-1-(4-fluoro-cyclohexyl)-pyrrolidin-2-one (Preparation 26) (190 mg, 1.03 mmol) in 5 mL dry THF, add 1.29 mL of 2M LDA (2.5 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 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-cb5c3a543dd24ceba7aeb9e3e54c65f9
Source dataset
uspto-grants-2011_08
Patent number
US07998999B2

Reaction notes

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