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Sulfuric Acid → Methyl-trans-1-[bis(4-methoxyphenyl)methyl]-6-oxo-4-(2,4,5-trifluorophenyl)piperidine-3-carboxylate

HRID 548607
Notes
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Reaction equation

HRID 548607 reaction equation
[CH3:1][O:2][C:3]([C@H:5]1[C@H:10]([C:11]2[CH:16]=[C:15]([F:17])[C:14]([F:18])=[CH:13][C:12]=2[F:19])[CH2:9][C:8](=[O:20])[NH:7][CH2:6]1)=[O:4].[CH3:21][O:22][C:23]1[CH:38]=[CH:37][C:26]([CH:27](O)[C:28]2[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=2)=[CH:25][CH:24]=1.S(=O)(=O)(O)O>C(O)(=O)C>[CH3:1][O:2][C:3]([C@H:5]1[C@H:10]([C:11]2[CH:16]=[C:15]([F:17])[C:14]([F:18])=[CH:13][C:12]=2[F:19])[CH2:9][C:8](=[O:20])[N:7]([CH:27]([C:26]2[CH:37]=[CH:38][C:23]([O:22][CH3:21])=[CH:24][CH:25]=2)[C:28]2[CH:29]=[CH:30][C:31]([O:34][CH3:35])=[CH:32][CH:33]=2)[CH2:6]1)=[O:4]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 69768p,p'-Dimethoxybenzhydryl alcoholHCID 66790341HCID 66790341, compound

Product 1

HCID 86617465Methyl-trans-1-[bis(4-methoxyphenyl)methyl]-6-oxo-4-(2,4,5-trifluorophenyl)piperidine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a stirred solution of 6.6 g (23 mmol) of the product of Step C in 100 mL of acetic acid was added 6.11 g (25 mmol) of 4,4′-dimethoxybenzhydrol followed by 5 mL of concentrated sulfuric acid and the resulting solution was stirred at ambient temperature for 18 h. The solution was then concentrated and cooled 0° C. before quenching with ice water (100 mL). The resulting mixture was extracted with three 300-mL portions of ethyl acetate, and the organic phases combined and washed sequentially with water, saturated aqueous sodium bicarbonate solution, and saturated aqueous brine (200 mL each). The organic phase was dried over magnesium sulfate, filtered, and evaporated in vacuo to yield a viscous oil. The crude material was purified by flash chromatography on a Biotage Horizon® system (silica gel, 0 to 50% ethyl acetate/hexanes gradient) to give methyl-trans-1-[bis(4-methoxyphenyl)methyl]-6-oxo-4-(2,4,5-trifluorophenyl)piperidine-3-carboxylate as a colorless solid. LC/MS 536.2 (M+23).

Workup

  1. concentrationThe solution was then concentrated
  2. temperaturecooled 0° C.
  3. custombefore quenching with ice water (100 mL)
  4. extractionThe resulting mixture was extracted with three 300-mL portions of ethyl acetate
  5. washwashed sequentially with water, saturated aqueous sodium bicarbonate solution, and saturated aqueous brine (200 mL each)
  6. dry with materialThe organic phase was dried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated in vacuo
  9. customto yield a viscous oil
  10. customThe crude material was purified by flash chromatography on a Biotage Horizon® system (silica gel, 0 to 50% ethyl acetate/hexanes gradient)

Sources & evidence

ORD record
ord-0d975d04298141f5a112c8565d8ab87a
Source dataset
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07943615B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes