m-Chloroperbenzoic acid → HCID 86597427, compound

HRID 556971Notes

Reaction equation

HRID 556971 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].ClC1C=CC=C(C(OO)=[O:29])C=1>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][C:11]2([C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=3)[CH:12]([O:29]2)[CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 157514251,1-Dimethylethyl 4-(4-chlorophenyl)-3,6-dihydro-1(2H)-pyridinecarboxylate

Product 1

HCID 86597427HCID 86597427, compoundYield 65.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-(4-chloro-phenyl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (4.0 g, 13.6 mmol) in CH2Cl2 (136 mL) cooled to 0° C. 3-Chloroperbenzoic acid (4.07 g, 20.4 mmol) was dissolved in CH2Cl2 and added portion wise over 45 min. A white precipitate was observed. The solution was allowed to stir at room temperature for 14 h. The reaction was washed with 1×10% NaSO3, 1×10% Na2CO3, 1× brine and dried over Mg2SO4, filtered and evaporated in vacuo. The residue was purified by Biotage flash system (90% hexane/10% ethyl acetate to 80% hexane/20% ethyl acetate to yield the title compound as a colorless oil (2.75 g, 65%). 1H-NMR (CDCl3) δ: 1.50 (9H, s), 2.15 (1H, m), 3.15 (2H, m), 3.6-4.2 (4H, m), 7.31 (4H, s).

Workup

  1. additionadded portion wise over 45 min
  2. washThe reaction was washed with 1×10% NaSO3, 1×10% Na2CO3, 1× brine
  3. dry with materialdried over Mg2SO4
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customThe residue was purified by Biotage flash system (90% hexane/10% ethyl acetate to 80% hexane/20% ethyl acetate

Sources & evidence

ORD record
ord-c8a79f47058a4ddabcc9d3e5c373e486
Source dataset
uspto-grants-2011_11
Patent number
US08058287B2

Reaction notes

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