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N,N,N',N'-Tetramethylethylenediamine → [3,5-difluoro-4-(tetrahydro-4-hydroxy-2H-thiopyran-4-yl)phenyl]carbamic Acid, 1-methylethyl Ester

HRID 2211689
Notes
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Reaction equation

HRID 2211689 reaction equation
C([Li])CCC.[CH:6]([O:9][C:10](=[O:20])[NH:11][C:12]1[CH:17]=[C:16]([F:18])[CH:15]=[C:14]([F:19])[CH:13]=1)([CH3:8])[CH3:7].CN(C)CCN(C)C.[S:29]1[CH2:34][CH2:33][C:32](=[O:35])[CH2:31][CH2:30]1>C1COCC1>[F:18][C:16]1[CH:17]=[C:12]([NH:11][C:10](=[O:20])[O:9][CH:6]([CH3:8])[CH3:7])[CH:13]=[C:14]([F:19])[C:15]=1[C:32]1([OH:35])[CH2:33][CH2:34][S:29][CH2:30][CH2:31]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 66173Tetrahydrothiopyran-4-oneHCID 58978077Isopropyl 3,5-difluoro-phenylcarbamateHCID 178418339Butyllithium

Product 1

HCID 86598977[3,5-difluoro-4-(tetrahydro-4-hydroxy-2H-thiopyran-4-yl)phenyl]carbamic Acid, 1-methylethyl Ester

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent
2×

Procedure

n-Butyllithium (2.5M in hexanes, 57.2 mL, 0.143 mol) was added dropwise with stirring at −78° C. to (3,5-difluoro-phenyl)-carbamic acid isopropyl ester (15.0 g, 0.07 mol) and N,N,N′,N′-tetramethylethylenediamine (21.04 mL, 0.139 mol) in THF (150 mL), and stirred for 20 min at this temperature. Tetrahydrothiopyran-4-one (8.50 g, 0.073 mol) dissolved in THF (10 mL) was then added dropwise at −78° C., stirred for 1 h, and then allowed to warm to room temperature. The reaction was stirred for another hour and then quenched with saturated aqueous ammonium chloride (100 mL). The reaction mixture was extracted with ethyl acetate, the extracts washed with brine, dried (MgSO4), and evaporated. The residue was purified by flash column chromatography (30% ethyl acetate/hexane) to give the title compound as white solid.

Workup

  1. additionwas then added dropwise at −78° C.
  2. stirringstirred for 1 h
  3. stirringThe reaction was stirred for another hour
  4. customquenched with saturated aqueous ammonium chloride (100 mL)
  5. extractionThe reaction mixture was extracted with ethyl acetate
  6. washthe extracts washed with brine
  7. dry with materialdried (MgSO4)
  8. customevaporated
  9. customThe residue was purified by flash column chromatography (30% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-118f42b147454f878e37e6dc9239ee19
Source dataset
uspto-grants-2006_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07101874B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes