Sulfuric Acid → HCID 57889422, compound

HRID 1820236Notes

Reaction equation

HRID 1820236 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@:8]2(O)[CH2:13][CH2:12][N:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:10][C:9]2([CH3:20])[CH3:19])=[CH:4][CH:3]=1.S(=O)(=O)(O)[OH:23].[C:27](#[N:29])[CH3:28]>>[C:27]([NH:29][C:8]1([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[CH2:13][CH2:12][N:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:10][C:9]1([CH3:20])[CH3:19])(=[O:23])[CH3:28]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 6342AcetonitrileHCID 57888831HCID 57888831, compound

Product 1

HCID 57889422HCID 57889422, compoundYield 67.2%

Procedure

A suspension of (R)-ethyl 4-(4-chlorophenyl)-4-hydroxy-3,3-dimethylpiperidine-1-carboxylate (322 mg, 1.033 mmol) in acetonitrile (3 mL) was treated with sulfuric acid (0.275 mL, 5.16 mmol), and the resulting clear solution was stirred overnight at room temperature. The reaction was quenched with saturated sodium carbonate, and then extracted 3× with ethyl acetate. The combined organic phases were washed with brine, dried over sodium sulfate, and concentrated in-vacuo. The residue was purified over silica gel, eluting with ethyl acetate/hexanes (10%-25%-100% EtOAc) to yield the title compound (245 mg, 0.694 mmol, 67.2% yield) as a colorless foam.

Workup

  1. customThe reaction was quenched with saturated sodium carbonate
  2. extractionextracted 3× with ethyl acetate
  3. washThe combined organic phases were washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in-vacuo
  6. customThe residue was purified over silica gel
  7. washeluting with ethyl acetate/hexanes (10%-25%-100% EtOAc)

Sources & evidence

ORD record
ord-08f731ef89334ea08bfbd4c9043a73f8
Source dataset
uspto-grants-2009_10
Patent number
US07601844B2

Reaction notes

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