HCID 59364405, compound → HCID 67350622, compound

HRID 1670895Notes

Reaction equation

HRID 1670895 reaction equation
Br[CH:2]1[CH:8]([Br:9])[CH2:7][CH:6]2[C@@H:3]1[CH2:4][C:5]2=[O:10].[C:11]([Si:15]([CH3:29])([CH3:28])[O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][NH:26][CH3:27])([CH3:14])([CH3:13])[CH3:12]>CC(C)=O>[Br:9][CH:8]1[CH2:7][C@H:6]2[C@H:3]([N:26]([CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][O:16][Si:15]([C:11]([CH3:14])([CH3:13])[CH3:12])([CH3:29])[CH3:28])[CH3:27])[C@@H:2]1[CH2:4][C:5]2=[O:10]

Participants

4

Reactant 2

HCID 59364405HCID 59364405, compoundHCID 67350563HCID 67350563, compound

Product 1

HCID 67350622HCID 67350622, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of (1S)-2,3-dibromo-bicyclo[3.2.0]heptan-6-one (2.15 g, 8.02 mmol) in acetone (20 mL) was added [9-(tert-butyl-dimethyl-silanyloxy)-nonyl]-methyl-amine (5.77 g, 12.3 mmol) and the reaction mixture was stirred at RT for 3 days. After evaporation of the solvent the residue was taken up in diethyl ether/ethyl acetate and washed with a satd NaHCO3 (aq)/brine mixture. The aqueous layer was extracted with diethyl ether. The combined organic layers were dried (Na2SO4), filtered, and concentrated to dryness to afford a dark brown oil, which was purified by column chromatography over silica gel using a gradient of 5-15% diethyl ether/pentane as eluent. After evaporation of the volatiles the title compound was obtained as a light yellow/brown oil.

Workup

  1. customAfter evaporation of the solvent the residue
  2. washwashed with a satd NaHCO3 (aq)/brine mixture
  3. extractionThe aqueous layer was extracted with diethyl ether
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated to dryness
  7. customto afford a dark brown oil, which
  8. customwas purified by column chromatography over silica gel using a gradient of 5-15% diethyl ether/pentane as eluent
  9. customAfter evaporation of the volatiles the title compound
  10. customwas obtained as a light yellow/brown oil

Sources & evidence

ORD record
ord-6b5b4b14c89646a7bdd9421c4e99ffc0
Source dataset
uspto-grants-2011_08
Patent number
US07994211B2

Reaction notes

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