Diethyl cyclopropane-1,1-dicarboxylate → HCID 68956592, compound

HRID 2378072Notes

Reaction equation

HRID 2378072 reaction equation
C([Li])CCC.[C:6]([Si:10]([CH3:29])([CH3:28])[O:11][C:12]1[CH:17]=[CH:16][C:15]([C:18](=[N:26][OH:27])[CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:14][CH:13]=1)([CH3:9])([CH3:8])[CH3:7].[C:30]1([C:38](OCC)=[O:39])([C:33]([O:35][CH2:36][CH3:37])=[O:34])[CH2:32][CH2:31]1>C1COCC1>[CH2:36]([O:35][C:33]([C:30]1([C:38]2([OH:39])[O:27][N:26]=[C:18]([C:15]3[CH:16]=[CH:17][C:12]([O:11][Si:10]([C:6]([CH3:7])([CH3:9])[CH3:8])([CH3:29])[CH3:28])=[CH:13][CH:14]=3)[CH:19]2[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH2:32][CH2:31]1)=[O:34])[CH3:37]

Participants

5

Reactant 3

HCID 73790Diethyl cyclopropane-1,1-dicarboxylateHCID 72579577HCID 72579577, compoundHCID 178418339Butyllithium

Product 1

HCID 68956592HCID 68956592, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

n-Butyllithium (2.5 M in hexane, 983.8 mL) is added to a solution of 1-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-2-phenyl-ethanone oxime, which may be produced as in Example 136 (400 g) in THF (4 L) at 0° C. and the reaction solution is stirred for one hour at this temperature. Diethyl 1,1-cyclopropanedicarboxylate (227 mL) is added to the reaction solution, stirred for one hour at 0° C. and then the reaction is quenched with saturated ammonium chloride, diluted with ethyl acetate, washed with water, brine, dried over anhydrous sodium sulfate, filtered, and the filtrate evaporated under reduced pressure. The crude product is purified by column chromatography with 5-10% ethyl acetate in hexane to give a light yellow solid, which is triturated with pentane and filtered to give 1-{3-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-5-hydroxy-4-phenyl-4,5-dihydro-isoxazol-5-yl}-cyclopropanecarboxylic acid ethyl ester (230.8 g.)

Workup

  1. stirringstirred for one hour at 0° C.
  2. customthe reaction is quenched with saturated ammonium chloride
  3. additiondiluted with ethyl acetate
  4. washwashed with water, brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customthe filtrate evaporated under reduced pressure
  8. customThe crude product is purified by column chromatography with 5-10% ethyl acetate in hexane
  9. customto give a light yellow solid, which
  10. customis triturated with pentane
  11. filtrationfiltered

Sources & evidence

ORD record
ord-d550e11fe0204cedb1cd8de31ba8aa84
Source dataset
uspto-grants-2008_12
Patent number
US07470715B2

Reaction notes

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