Sodium Iodide → (4S,5S)-4-[(Benzyloxy)methyl]-5-(iodomethyl)-2,2-dimethyl-1,3-dioxolane

HRID 1695019Notes

Reaction equation

CS(O[CH2:6][C@H:7]1[C@H:11]([CH2:12][O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[O:10][C:9]([CH3:22])([CH3:21])[O:8]1)(=O)=O.[I-:23].[Na+]>C(#N)C>[CH2:14]([O:13][CH2:12][C@H:11]1[C@@H:7]([CH2:6][I:23])[O:8][C:9]([CH3:22])([CH3:21])[O:10]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of 46.19 g of the crude {(4S,5S)-5-[(benzyloxy)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl}methyl methanesulfonate obtained in Reference Example (1b) (140 mmol) and 62.87 g of sodium iodide (419 mmol) in acetonitrile (420 ml) was stirred at 80° C. for 22 hours. The reaction mixture was cooled and then concentrated under reduced pressure and diluted with water, followed by extraction with ethyl acetate. Then, the organic layer was washed with a 1.5 M sodium sulfite aqueous solution, water and brine and dried over anhydrous magnesium sulfate. After filtration, the solvent was evaporated under reduced pressure to obtain 49.20 g of the crude title compound.

Workup

temperatureThe reaction mixture was cooled
concentrationconcentrated under reduced pressure
additiondiluted with water
extractionfollowed by extraction with ethyl acetate
washThen, the organic layer was washed with a 1.5 M sodium sulfite aqueous solution, water and brine
dry with materialdried over anhydrous magnesium sulfate
filtrationAfter filtration
customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record: ord-719b9f5962c04e8f9d619a99a23a8704
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08158790B2

Reaction notes

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