m-Chloroperbenzoic acid → HCID 86755278, compound

HRID 1003385Notes

Reaction equation

HRID 1003385 reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[CH:12]([C@@H:15]1[CH2:20][CH2:19][C@@H:18]([CH3:21])[CH2:17][C@H:16]1[O:22][CH2:23][C:24]([O:26][CH2:27][CH:28]1[CH:33]=[CH:32][CH2:31][N:30]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:29]1)=[O:25])([CH3:14])[CH3:13]>C(Cl)Cl>[CH:12]([C@@H:15]1[CH2:20][CH2:19][C@@H:18]([CH3:21])[CH2:17][C@H:16]1[O:22][CH2:23][C:24]([O:26][CH2:27][CH:28]1[CH:33]2[O:6][CH:32]2[CH2:31][N:30]([C:34]([O:36][C:37]([CH3:40])([CH3:38])[CH3:39])=[O:35])[CH2:29]1)=[O:25])([CH3:14])[CH3:13]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acid2×HCID 70296923HCID 70296923, compound

Product 1

HCID 86755278HCID 86755278, compoundYield 66.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-chloroperoxybenzoic acid (0.9 g, 5.2 mmol), tert-butyl 3-((1R,2S,5R)-2-isopropyl-5-methyl-1-cyclohexyloxy)acetoxymethyl-1,2,3,6-tetrahydropyridine-1-carboxylate (0.5 g, 1.2 mmol), and methylene chloride (150 ml) was stirred at room temperature for 20 h. An extra portion of 3-chloroperoxybenzoic acid (1.1 eq) was added and the mixture refluxed for 2h. The reaction mixture was extracted with 1M sodium hydroxide and water, dried over magnesium sulphate and evaporated to dryness in vacuo. The residue was purified on a silica gel column (Eluent: heptane/ethyl acetate (5/1)) to give tert-butyl 3-((1R,2S,5R) 2-isopropyl-5-methyl-1-cyclohexyloxy)acetoxymethyl-4,5-epoxypiperidine-1-carboxylate as an oil (Yield: 0.34 g, 66%).

Workup

  1. temperaturethe mixture refluxed for 2h
  2. extractionThe reaction mixture was extracted with 1M sodium hydroxide and water
  3. dry with materialdried over magnesium sulphate
  4. customevaporated to dryness in vacuo
  5. customThe residue was purified on a silica gel column (Eluent: heptane/ethyl acetate (5/1))

Sources & evidence

ORD record
ord-fbfc1e0d8a6c41ccaa30eb4ac7811dd0
Source dataset
uspto-grants-2000_04
Patent number
US06046214

Reaction notes

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