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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 1816440
Notes
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Reaction equation

HRID 1816440 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-475a1e757a554d419c52036850924373
Source dataset
uspto-grants-2005_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06884813B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes