Trichloroacetic Acid → Tert-butyl 4-(2,2,2-trichloro-1-hydroxyethyl)piperidine-1-carboxylate

HRID 335151Notes

Reaction equation

HRID 335151 reaction equation
[Cl:1][C:2]([Cl:7])([Cl:6])[C:3](O)=[O:4].ClC(Cl)(Cl)C([O-])=O.[Na+].C([CH:18]1[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][CH2:19]1)=O>CN(C=O)C>[Cl:1][C:2]([Cl:7])([Cl:6])[CH:3]([CH:18]1[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][CH2:19]1)[OH:4]

Participants

5

Reactant 3

HCID 6421Trichloroacetic AcidHCID 1514430tert-Butyl 4-formylpiperidine-1-carboxylateHCID 23681045Sodium Trichloroacetate

Product 1

HCID 66995190Tert-butyl 4-(2,2,2-trichloro-1-hydroxyethyl)piperidine-1-carboxylateYield 73.53%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Placed 2,2,2-trichloroacetic acid (5.746 g, 35.17 mmol) in DMF (5 mL) and added slowly sodium 2,2,2-trichloroacetate (6.519 g, 35.17 mmol). The reaction was stirred for 10 minutes and tert-butyl 4-formylpiperidine-1-carboxylate (5.00 g, 23.44 mmol) was added. The reaction was stirred for 40 minutes then quenched with saturated sodium bicarbonate and filtered. The solids were washed with water and dried. The product was triturated with water and filtered to give the title compound (5.734 g, 73.53% yield).

Workup

  1. stirringThe reaction was stirred for 40 minutes
  2. customthen quenched with saturated sodium bicarbonate
  3. filtrationfiltered
  4. washThe solids were washed with water
  5. customdried
  6. customThe product was triturated with water
  7. filtrationfiltered

Sources & evidence

ORD record
ord-44525c02643246d18d8d15ecd0a16944
Source dataset
uspto-grants-2014_11
Patent number
US08883828B2

Reaction notes

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