Tert-Butanesulfinamide → HCID 58562506, compound

HRID 1896815Notes

Reaction equation

HRID 1896815 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([CH:11]=O)[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.[CH3:13][C:14]([S:17]([NH2:19])=[O:18])([CH3:16])[CH3:15]>C1COCC1.C(OCC)(=O)C.[O-]CC.[Ti+4].[O-]CC.[O-]CC.[O-]CC>[O:4]1[C:5]2([CH2:6][CH2:7][CH:8](/[CH:11]=[N:19]/[S:17]([C:14]([CH3:16])([CH3:15])[CH3:13])=[O:18])[CH2:9][CH2:10]2)[O:1][CH2:2][CH2:3]1

Participants

6

Reactant 2

HCID 3382465Tert-ButanesulfinamideHCID 98989471,4-Dioxaspiro(4.5)decane-8-carbaldehyde

Product 1

HCID 58562506HCID 58562506, compound

Reagents, catalysts & solvents 3

HCID 76524Titanium tetraethoxideCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1,4-dioxaspiro[4.5]decane-8-carbaldehyde (6.68 g, 39.2 mmol, prepared as described in Pearson, et al. in J. Org. Chem. 1997, 62(16), 5284-5292), racemic 2-methylpropane-2-sulfinamide (3.50 g, 28.0 mmol), tech grade titanium (IV) ethoxide (14 mL, 67.5 mmol) were dissolved in dry THF (100 mL), placed under an argon atmosphere and stirred at ambient temperature for 16 hours. The next day the reaction mixture was diluted with ethyl acetate and poured onto rapidly stirred ice cold brine. The copious white precipitate was removed by filtration through celite and the organic layer removed. After drying over Na2SO4 and concentration the residue was purified by flash chromatography (silica gel, 0-100% ether/DCM) to afford the product.

Workup

  1. additionpoured onto rapidly stirred ice cold brine
  2. customThe copious white precipitate was removed by filtration through celite
  3. customthe organic layer removed
  4. dry with materialAfter drying over Na2SO4 and concentration the residue
  5. customwas purified by flash chromatography (silica gel, 0-100% ether/DCM)
  6. customto afford the product

Sources & evidence

ORD record
ord-8ae12e4128b54b788c0215a10402b7c4
Source dataset
uspto-grants-2013_08
Patent number
US08518969B2

Reaction notes

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