Bromide ion → N-(1-(1,4-dioxaspiro[4.5]decan-8-yl)but-3-en-1-yl)-2-methylpropane-2-sulfinamide

HRID 2175499Notes

Reaction equation

HRID 2175499 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.[Br-].[CH2:20]1[CH2:24]OC[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])[CH2:24][CH:20]=[CH2:21])[CH2:9][CH2:10]2)[O:4][CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 259Bromide ionHCID 8028TetrahydrofuranHCID 58562506HCID 58562506, compound

Product 1

HCID 58562759N-(1-(1,4-dioxaspiro[4.5]decan-8-yl)but-3-en-1-yl)-2-methylpropane-2-sulfinamide

Procedure

A solution (E)-N-(1,4-dioxaspiro[4.5]decan-8-ylmethylene)-2-methylpropane-2-sulfinamide (1.91 g, 6.99 mmol), prepared in the previous step, in dry THF (48 mL) was treated with a solution of allylmagnesiumm bromide (10.5 mL, 21 mmol, 2N 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-da38009224144fc7b8d06cfe4d946583
Source dataset
uspto-grants-2015_06
Patent number
US09062048B2

Reaction notes

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