1,4-Dioxaspiro[4.5]decan-8-one → HCID 59556157, compound

HRID 2388344Notes

Reaction equation

HRID 2388344 reaction equation
[Li]CCCC.[CH3:6][O:7][C:8](=[O:15])[NH:9][C:10]1[S:11][CH:12]=[CH:13][N:14]=1.[O:16]1[C:20]2([CH2:25][CH2:24][C:23](=[O:26])[CH2:22][CH2:21]2)[O:19][CH2:18][CH2:17]1>C1COCC1>[CH3:6][O:7][C:8](=[O:15])[NH:9][C:10]1[S:11][C:12]([C:23]2([OH:26])[CH2:24][CH2:25][C:20]3([O:19][CH2:18][CH2:17][O:16]3)[CH2:21][CH2:22]2)=[CH:13][N:14]=1

Participants

5

Reactant 3

HCID 5674151,4-Dioxaspiro[4.5]decan-8-oneHCID 686488HCID 686488, compoundHCID 178418339Butyllithium

Product 1

HCID 59556157HCID 59556157, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

A solution of n-BuLi (2.5 M in hexanes, 28 mL, 70 mmol) was dropped slowly into a solution of thiazol-2-yl-carbamic acid methyl ester (Aldrich, 5.0 g, 31.6 mmol) in THF (100 mL) at −78° C., over 10 min. The reaction was stirred for additional 20 min. at −78° C. A solution of 1,4-dioxa-spiro[4.5]decan-8-one (Aldrich, 7.0 g, 45 mmol) in THF (20 mL) was slowly dropped into the reaction. After addition, the reaction was stirred for an additional 2 hours at −78° C. The reaction was then quenched with diluted NH4Cl solution and warmed to room temperature. The solvent was removed in vacuo and the residue was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and concentrated to give a yellow solid, which was then purified by silica gel column on a CombiFlash® system using hexanes and ethyl acetate (from 10% ethyl acetate to 100% ethyl acetate) to afford the title compound as a white solid.

Workup

  1. additionAfter addition
  2. stirringthe reaction was stirred for an additional 2 hours at −78° C
  3. customThe reaction was then quenched with diluted NH4Cl solution
  4. temperaturewarmed to room temperature
  5. customThe solvent was removed in vacuo
  6. customthe residue was partitioned between ethyl acetate and water
  7. washThe organic layer was washed with brine
  8. dry with materialdried over anhydrous Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customto give a yellow solid, which
  12. customwas then purified by silica gel column on a CombiFlash® system

Sources & evidence

ORD record
ord-3e58d580d25a4e998c1263f4e5f2254a
Source dataset
uspto-grants-2012_09
Patent number
US08269015B2

Reaction notes

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