Hydrogen Peroxide → 1-[2-(Tert-butoxycarbonyl)-3-(2-methoxyethoxy)propyl]-1-cyclopentanecarboxylic acid

HRID 374338Notes

Reaction equation

HRID 374338 reaction equation
[C:1]([C:4]1([CH2:11][CH:12]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:13][O:14][CH2:15][CH2:16][O:17][CH3:18])[CH2:9][CH2:8][CH2:7][CH2:6]C1=O)(=[O:3])C.[OH:26]O>C(O)(C)(C)C.S(=O)(=O)(O)O>[C:22]([O:21][C:19]([CH:12]([CH2:13][O:14][CH2:15][CH2:16][O:17][CH3:18])[CH2:11][C:4]1([C:1]([OH:26])=[O:3])[CH2:9][CH2:8][CH2:7][CH2:6]1)=[O:20])([CH3:25])([CH3:24])[CH3:23]

Participants

5

Reactant 2

HCID 784Hydrogen PeroxideHCID 10915277HCID 10915277, compound

Product 1

HCID 110674891-[2-(Tert-butoxycarbonyl)-3-(2-methoxyethoxy)propyl]-1-cyclopentanecarboxylic acidYield 105.9%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 6386tert-ButanolSolvent

Procedure

To a solution of 2-acetyl-2-[2-(tert-butoxycarbonyl)-3-(2-methoxyethoxy)propyl]cyclohexanone (see Preparations 5 and 11) (50 m9, 0.14 mmol) in tert-butanol (0.5 ml) was added a 30% aqueous hydrogen peroxide solution (0.02 ml, 0.168 mmol) and concentrated sulphuric acid (one drop) at room temperature. The mixture was stirred at room temperature for 4 hours, partitioned between dichloromethane (10 ml) and water (10 ml), and the layers separated. The aqueous layer was extracted with dichloromethane (2×10 ml), the combined organic extracts dried over magnesium sulphate, filtered and concentrated under reduced pressure to give the title compound, (49 mg). Rf. 0.36 (silica, ethyl acetate). 1H-NMR (300 MHz, CDCl3) =1.43 (s, 9H), 1.43-1.60 (m, 2H), 1.61-1.65 (m, 4H), 1.78 (dd, 1H), 2.0 (dd, 1H), 2.08-2.20 (m, 2H), 2.59-2.70 (m, 1H), 3.38 (s, 3H), 3.48-3.65 (m, 6H) ppm.

Workup

  1. custompartitioned between dichloromethane (10 ml) and water (10 ml)
  2. customthe layers separated
  3. extractionThe aqueous layer was extracted with dichloromethane (2×10 ml)
  4. dry with materialthe combined organic extracts dried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d4388147f52143668e061f5a9ee8003e
Source dataset
uspto-grants-1992_11
Patent number
US05166406

Reaction notes

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