Chloride → HCID 68003945, compound

HRID 1896818Notes

Reaction equation

HRID 1896818 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.[Cl-].[CH2:20]1COC[CH2:21]1>>[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])[CH:20]=[CH2:21])[CH2:9][CH2:10]2)[O:4][CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 312ChlorideHCID 8028TetrahydrofuranHCID 58562506HCID 58562506, compound

Product 1

HCID 68003945HCID 68003945, compound

Procedure

A solution (E)-N-(1,4-dioxaspiro[4.5]decan-8-ylmethylene)-2-methylpropane-2-sulfinamide (1.89 g, 5.53 mmol), prepared in Example 11, step A, in dry THF (48 mL) was treated with a solution of vinylmagnesiumm chloride (10.4 mL, 16.6 mmol, 1.6 N in THF) dropwise at ambient temperature under argon. After the complete addition, the reaction mixture was allowed to stir at room temperature and for 3 hours and then quenched at 0° C. by the cautious addition of saturated ammonium chloride solution. After extraction with ethyl acetate, the organic layer was concentrated in vacuo and the residue purified by flash chromatography (silica gel, 0-5% MeOH/Ethyl Acetate) to afford the product as a mixture of disatereomers.

Workup

  1. additionAfter the complete addition
  2. customquenched at 0° C. by the cautious addition of saturated ammonium chloride solution
  3. extractionAfter extraction with ethyl acetate
  4. concentrationthe organic layer was concentrated in vacuo
  5. customthe residue purified by flash chromatography (silica gel, 0-5% MeOH/Ethyl Acetate)
  6. customto afford the product
  7. additionas a mixture of disatereomers

Sources & evidence

ORD record
ord-5e32fa7b1ecc4c58b6e55bf5e21e5a76
Source dataset
uspto-grants-2013_08
Patent number
US08518969B2

Reaction notes

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