1,4-Dioxaspiro[4.5]decan-8-one → N-(1,4-dioxaspiro[4.5]dec-8-ylidene)-2-methylpropane-2-sulfinamide

HRID 1893324Notes

Reaction equation

HRID 1893324 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][C:8](=O)[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.[CH3:12][C:13]([S:16]([NH2:18])=[O:17])([CH3:15])[CH3:14]>C1COCC1>[O:1]1[C:5]2([CH2:10][CH2:9][C:8](=[N:18][S:16]([C:13]([CH3:15])([CH3:14])[CH3:12])=[O:17])[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 5674151,4-Dioxaspiro[4.5]decan-8-oneHCID 3382465Tert-Butanesulfinamide

Product 1

HCID 59733754N-(1,4-dioxaspiro[4.5]dec-8-ylidene)-2-methylpropane-2-sulfinamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1,4-dioxa-spiro[4.5]decan-8-one (Aldrich, 4.07 g, 26.1 mmol) and 2-methyl-propane-2-sulfinic acid amide (Aldrich, 3.16 g, 26.1 mmol) in THF (20 mL) was added Ti(OEt)4 (Aldrich, 10.8 mL, 52.2 mmol) at room temperature. The reaction was stirred overnight and quenched with ˜5 mL water until precipitation completed. The solid was filtered off and washed with additional ethyl acetate. The combined filtrate was dried over anhydrous Na2SO4, filtered, concentrated and the residue was purified by a CombiFlash® system using hexanes and ethyl acetate as eluent (from pure hexanes to pure ethyl acetate) to afford the title compound as colorless oil.

Workup

  1. customquenched with ˜5 mL water until precipitation
  2. filtrationThe solid was filtered off
  3. washwashed with additional ethyl acetate
  4. dry with materialThe combined filtrate was dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customthe residue was purified by a CombiFlash® system

Sources & evidence

ORD record
ord-92ddf2f7d8324f37bdecb90d5eeba399
Source dataset
uspto-grants-2013_08
Patent number
US08513229B2

Reaction notes

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