Lithium Hydroxide → HCID 11579987, compound

HRID 2103017Notes

Reaction equation

HRID 2103017 reaction equation
C(O[C:5]1([NH:21][O:22][CH3:23])[C:17]2[C:12](=[C:13]([CH3:20])[C:14]([CH3:19])=[CH:15][C:16]=2[CH3:18])[O:11][C:7]2([CH2:10][CH2:9][CH2:8]2)[CH2:6]1)(=O)C.[OH-].[Li+].C(OCC)(=[O:28])C>CO>[CH3:23][O:22][NH:21][CH:5]1[C:17]2[C:12](=[C:13]([CH3:20])[C:14]([CH3:19])=[C:15]([OH:28])[C:16]=2[CH3:18])[O:11][C:7]2([CH2:8][CH2:9][CH2:10]2)[CH2:6]1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 8857Ethyl AcetateHCID 86605479HCID 86605479, compound

Product 1

HCID 11579987HCID 11579987, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (4-(methoxyamino)-5,7,8-trimethyl-3,4-dihydrospiro[chromene-2,1′-cyclobutan]-4-yl acetate) (80 mg) in methanol (8 mL) was added lithium hydroxide (4%) water solution under nitrogen. The solution was stirred at room temperature for 2 hours. Ethyl acetate was added. The organic layer was washed with ammonium hydrochloride water solution, water and brine. The solution was evaporated and chromatographed (silica gel, hexane-ethyl acetate 2% to 8%) to give 70 mg of 4-(methoxyamino)-5,7,8-trimethyl-3,4-dihydrospiro[chromene-2,1′-cyclobutan]-6-ol.

Workup

  1. washThe organic layer was washed with ammonium hydrochloride water solution, water and brine
  2. customThe solution was evaporated
  3. customchromatographed (silica gel, hexane-ethyl acetate 2% to 8%)

Sources & evidence

ORD record
ord-b14db87bc69f4a288f8b0578c412c08f
Source dataset
uspto-grants-2009_08
Patent number
US07576094B2

Reaction notes

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