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Lithium diisopropylamide → Trifluoro-methanesulfonic acid 3,5-dichloro-4-[1-(4,4-difluoro-cyclohexyl)-2-oxo-pyrrolidin-3-ylmethyl]-phenyl ester

HRID 1672734
Notes
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Reaction equation

HRID 1672734 reaction equation
[F:1][C:2]1([F:14])[CH2:7][CH2:6][CH: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.[Cl:23][C:24]1[CH:25]=[C:26]([O:37][S:38]([C:41]([F:44])([F:43])[F:42])(=[O:40])=[O:39])[CH:27]=[C:28]([Cl:36])[C:29]=1[CH2:30]OS(C)(=O)=O>C1COCC1>[Cl:23][C:24]1[CH:25]=[C:26]([O:37][S:38]([C:41]([F:43])([F:44])[F:42])(=[O:40])=[O:39])[CH:27]=[C:28]([Cl:36])[C:29]=1[CH2:30][CH:10]1[CH2:11][CH2:12][N:8]([CH:5]2[CH2:4][CH2:3][C:2]([F:1])([F:14])[CH2:7][CH2:6]2)[C:9]1=[O:13]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 2724682Lithium diisopropylamideHCID 57878591HCID 57878591, compoundHCID 86634570Trifluoro-methanesulfonic acid 3,5-dichloro-4-methanesulfonyloxymethyl-phenyl ester

Product 1

HCID 57878605Trifluoro-methanesulfonic acid 3,5-dichloro-4-[1-(4,4-difluoro-cyclohexyl)-2-oxo-pyrrolidin-3-ylmethyl]-phenyl ester

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent
2×

Procedure

To a solution of 1-(4,4-difluoro-cyclohexyl)-pyrrolidin-2-one (447 mg, 2.2 mmol) in 22 mL dry THF, add 1.76 mL of 2M LDA (1.2 eq.) in THF dropwise at −78° C. Then, add 1.24 g of trifluoro-methanesulfonic acid 3,5-dichloro-4-methanesulfonyloxymethyl-phenyl ester (1.4 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, then brine, and dry over Na2SO4, filter and concentrate. Purify the crude material by chromatography to afford the title compound: mass spectrum (m/z): 376 (M+1).

Workup

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

Sources & evidence

ORD record
ord-4077e4a8aafb471c9c02f11db51c5da0
Source dataset
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07998999B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes