Water → HCID 23149940, compound

HRID 2263510Notes

Reaction equation

HRID 2263510 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C:11]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[C:16]=2[F:22])(O)[CH2:10][CH2:9]1)=O)(C)(C)C.S(=O)(=O)(O)O.O.[OH-].[Na+]>C1(C)C=CC=CC=1>[F:22][C:16]1[C:17]([F:21])=[CH:18][CH:19]=[CH:20][C:15]=1[C:11]1[CH2:12][CH2:13][NH:8][CH2:9][CH:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 57438800HCID 57438800, compound

Product 1

HCID 23149940HCID 23149940, compoundYield 53.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of tert-butyl-4-(2,3-difluorophenyl)-4-hydroxypiperidine-1-carboxylate (7.48 g, 23.9 mmol) in toluene (50 ml) was added sulfuric acid (18 M, 1.33 ml, 23.9 mmol) and the mixture was refluxed under a Dean-Stark water separator. The mixture was poured on to ice and was basified with aqueous sodium hydroxide solution (15%). The mixture was extracted with ethylacetate (3×50 ml) and the combined organic phases was dried (MgSO4), filtered and evaporated to dryness. The residue was purified by flash column chromatography (MeOH) to give the title compound (2.5 g). MS m/z (rel. intensity, 70 eV) 195 (M+, bp), 194 (42), 166 (30), 151 (33), 127 (35).

Workup

  1. additionThe mixture was poured on to ice
  2. extractionThe mixture was extracted with ethylacetate (3×50 ml)
  3. dry with materialthe combined organic phases was dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe residue was purified by flash column chromatography (MeOH)

Sources & evidence

ORD record
ord-3459a9f6b5df49aba34647b38cad4996
Source dataset
uspto-grants-2010_12
Patent number
US07851629B2

Reaction notes

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