Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 86639729, compound

HRID 2192588Notes

Reaction equation

[N:1]([CH2:4][C@H:5]([CH3:22])[C@H:6]([C@H:15]1[CH2:19][O:18]C(C)(C)[O:16]1)[O:7][Si:8]([C:11]([CH3:14])([CH3:13])[CH3:12])([CH3:10])[CH3:9])=[N+:2]=[N-:3].CC1C=CC(S([O-])(=O)=O)=CC=1.C1C=C[NH+]=CC=1>CO>[N:1]([CH2:4][C@H:5]([CH3:22])[C@@H:6]([O:7][Si:8]([C:11]([CH3:14])([CH3:13])[CH3:12])([CH3:10])[CH3:9])[C@H:15]([OH:16])[CH2:19][OH:18])=[N+:2]=[N-:3]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of ((1R,2S)-3-azido-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-methylpropoxy)(tert-butyl)dimethylsilane (1.0 equiv.) in MeOH (0.1 M) was added PPTS (1.0 equiv.) and the mixture was stirred at rt for 14 hours, 50° C. for 2 hours and 80° C. for 1 hour. The volatiles were removed under vacuo and the residue was purified via silica gel column chromatography (10-25% EtOAc/n-heptanes) yielding (2R,3R,4S)-5-azido-3-(tert-butyldimethylsilyloxy)-4-methylpentane-1,2-diol (40%).

Workup

customThe volatiles were removed under vacuo
customthe residue was purified via silica gel column chromatography (10-25% EtOAc/n-heptanes)

Sources & evidence

ORD record: ord-8f136d10e4684730937728b871b03504
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08329732B2

Reaction notes

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