HCID 58562506, compound → HCID 58562811, compound

HRID 2175590Notes

Reaction equation

HRID 2175590 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][CH:8](/[CH:11]=[N:12]/[S:13]([C:15]([CH3:18])([CH3:17])[CH3:16])=[O:14])[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.[CH2:19]([Mg]Cl)[CH3:20]>C1COCC1>[O:1]1[C:5]2([CH2:6][CH2:7][CH:8]([CH:11]([NH:12][S:13]([C:15]([CH3:18])([CH3:17])[CH3:16])=[O:14])[CH2:19][CH3:20])[CH2:9][CH2:10]2)[O:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 58562506HCID 58562506, compoundHCID 178461633HCID 178461633, compound

Product 1

HCID 58562811HCID 58562811, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (E)-N-(1,4-dioxaspiro[4.5]decan-8-ylmethylene)-2-methylpropane-2-sulfinamide (as prepared in of Example 11 Step A, 3.66 g, 13.4 mmol) in dry THF (100 mL) was placed under an argon atmosphere and treated with ethylmagnesium chloride dropwise. After stirring at ambient temperature for 2 hours, the reaction mixture was cooled to −10° C. and cautiously quenched by the addition of saturated ammonium chloride solution. After dilution with water and ether extraction, the organic layer was concentrated in vacuo. Purification of the residue by flash chrom (silica gel, ethyl acetate) afforded the titled compound as a solid. 1H NMR (CHLOROFORM-d) δ: 3.80-4.00 (m, 4H), 2.85-3.15 (series of m, 2H), 1.71 (series of m, 11H), 1.20-1.25 (s, 9H), 0.97 (t, J=7.5 Hz, 3H)

Workup

  1. temperaturethe reaction mixture was cooled to −10° C.
  2. customcautiously quenched by the addition of saturated ammonium chloride solution
  3. extractionAfter dilution with water and ether extraction
  4. concentrationthe organic layer was concentrated in vacuo
  5. customPurification of the residue by flash chrom (silica gel, ethyl acetate)

Sources & evidence

ORD record
ord-e2f697c37ba24269a6ee9394f282abc0
Source dataset
uspto-grants-2015_06
Patent number
US09062048B2

Reaction notes

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