Water → [(3R,4R)-4-azidotetrahydrofuran-3-yl]oxy-tert-butyl-dimethyl-silane

HRID 245062Notes

Reaction equation

[Si:1]([O:8][C@@H:9]1[CH2:13][O:12][CH2:11][C@@H:10]1CS([O-])(=O)=O)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[N-:19]=[N+:20]=[N-:21].[Na+].O>CN(C=O)C.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[N:19]([C@@H:10]1[CH2:11][O:12][CH2:13][C@@H:9]1[O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])=[N+:20]=[N-:21]

Participants

Conditions

Temperature: 60 °C

Procedure

[(3S,4S)-4-(Tert-butyl(dimethyl)silyl)oxytetrahydrofuran-3-yl]methanesulfonate (3.00 g, 10.1 mmol) is dissolved in DMF (50 mL). Sodium azide (1.32 g, 20.2 mmol) is added and the reaction is heated to 60° C. for 72 h. Tetra-n-butylammonium iodide (0.400 g, 1.08 mmol) is added and the temperature is raised to 120° C. for 14 days. Water is added and the product is extracted into EtOAc. The organic layer is washed with water a second time and then dried over magnesium sulfate, filtered, and concentrated to give 2.9 g of crude product as a pale yellow oil. The crude product is purified on silica gel (120 g, 2-20% EtOAc/hexanes, observed on TLC with KMnO4 staining) to give the title compound as a colorless oil (1.3 g, 53%). GC-MS m/z 186 (M-tBu)+.

Workup

temperaturethe temperature is raised to 120° C. for 14 days
extractionthe product is extracted into EtOAc
washThe organic layer is washed with water a second time
dry with materialdried over magnesium sulfate
filtrationfiltered
concentrationconcentrated
customto give 2.9 g of crude product as a pale yellow oil
customThe crude product is purified on silica gel (120 g, 2-20% EtOAc/hexanes, observed on TLC with KMnO4 staining)

Sources & evidence

ORD record: ord-06eec2b12a0e4433aad2d54fa259c176
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08658693B2

Reaction notes

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