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Ammonium Chloride → 1-Tert-butoxycarbonyl-4-[2-(4-chloro-phenylsulfanyl)-5-trifluoromethyl-phenyl]-piperidine-4-ol

HRID 15229
Notes
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Reaction equation

HRID 15229 reaction equation
C([Li])CCC.Br[C:7]1[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:10]=[CH:9][C:8]=1[S:17][C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=1.[C:25]([O:29][C:30]([N:32]1[CH2:37][CH2:36][C:35](=[O:38])[CH2:34][CH2:33]1)=[O:31])([CH3:28])([CH3:27])[CH3:26].[Cl-].[NH4+]>C1COCC1>[C:25]([O:29][C:30]([N:32]1[CH2:37][CH2:36][C:35]([C:7]2[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:10]=[CH:9][C:8]=2[S:17][C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)([OH:38])[CH2:34][CH2:33]1)=[O:31])([CH3:28])([CH3:26])[CH3:27]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 686834131-Bromo-2-(4-chlorophenylsulfanyl)-5-(trifluoromethyl)benzeneHCID 178418339Butyllithium

Product 1

HCID 686846901-Tert-butoxycarbonyl-4-[2-(4-chloro-phenylsulfanyl)-5-trifluoromethyl-phenyl]-piperidine-4-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of n-butyl lithium (2.5 M in hexane, 6.5 mL, 16.2 mmol) was slowly added to a stirred solution of 1-bromo-2-(4-chlorophenylsulfanyl)-5-(trifluoromethyl)benzene (5.96 g, 16.2 mmol) in dry THF (40 mL) under argon at −78° C. The solution was stirred for 10 min before 4-oxo-piperidine-1-carboxylic acid tert-butyl ester (3.23 g, 16.2 mmol) was added in one portion. The solution was allowed to warm to rt and then stirred overnight. Saturated aqueous ammonium chloride (80 mL) was added and the solution was extracted with ethyl acetate (80 mL). The organic phase was washed with saturated aqueous sodium chloride (50 mL), dried over magnesium sulfate and the solvent was evaporated off. The crude product was purified by flash chromatography on silica gel (eluent: ethyl acetate/heptane 2:8) to produce the target compound as a white foam, yield: 4.53 g (57%).

Workup

  1. additionwas added in one portion
  2. extractionthe solution was extracted with ethyl acetate (80 mL)
  3. washThe organic phase was washed with saturated aqueous sodium chloride (50 mL)
  4. dry with materialdried over magnesium sulfate
  5. customthe solvent was evaporated off
  6. customThe crude product was purified by flash chromatography on silica gel (eluent: ethyl acetate/heptane 2:8)

Sources & evidence

ORD record
ord-e0a36d7253684b78aae29694191ea28d
Source dataset
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07732463B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes