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Ethyl Acetate → HCID 90029693, compound

HRID 2200128
Notes
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Reaction equation

HRID 2200128 reaction equation
C([Li])CCC.Br[C:7]1[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:10]=[C:9]([Br:17])[CH:8]=1.[N+](C1C=C[C:24]([C:27]2[CH2:32][CH2:31][N:30]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:29][CH:28]=2)=C(C(F)(F)F)C=1)([O-])=O.CC[O:46]C(C)=O>C1COCC1>[C:36]([O:35][C:33]([N:30]1[CH2:31][CH2:32][CH:27]([C:24](=[O:46])[C:7]2[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:10]=[C:9]([Br:17])[CH:8]=2)[CH2:28][CH2:29]1)=[O:34])([CH3:39])([CH3:38])[CH3:37]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 20634891,3-Dibromo-5-(trifluoromethyl)benzeneHCID 66711203HCID 66711203, compoundHCID 178418339Butyllithium

Product 1

HCID 90029693HCID 90029693, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Conditions

Temperature
-78 °C

Procedure

Add n-butyllithium (2.5 N, 1.44 mL) to the solution of 1,3-dibromo-5-(trifluoromethyl)benzene (1 g, 3.28 mmol) in THF (15 mL) at −78° C. and stir the mixture at −78° C. for 1 hr. Then add tert-butyl 4-(methoxy(methyl)carbamoyl) piperidine-1-carboxylate (1.4 g, 4.92 mmol) obtained in Step 1 to the mixture and continue stirring. TLC (PE:EtOAc=5:1) shows the reaction is complete. Quench the reaction mixture with saturated ammonium chloride solution. Partition between EtOAc and water, separate the organic layer, and wash with brine, dry over anhydrous sodium sulfate, concentrate to give the crude product. Purify by flash chromatography (silica gel, DCM:MeOH=20:1) to afford the product (387 mg, 27%). MS: (M+1): 436.

Workup

  1. customQuench the reaction mixture with saturated ammonium chloride solution
  2. customPartition between EtOAc and water
  3. customseparate the organic layer
  4. washwash with brine
  5. dry with materialdry over anhydrous sodium sulfate
  6. concentrationconcentrate
  7. customto give the crude product
  8. customPurify by flash chromatography (silica gel, DCM:MeOH=20:1)

Sources & evidence

ORD record
ord-b28f36bf2bec47a2b8a0f8b097babc33
Source dataset
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09359338B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes