Ammonium Chloride → [5-({[Tert-butyl(diphenyl)silyl]oxy}methyl)-1,3,4-thiadiazol-2-yl]methanol

HRID 1881931Notes

Reaction equation

[Si:1]([O:18][CH2:19][C:20]1[S:24][C:23]([C:25](OCC)=[O:26])=[N:22][N:21]=1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].[Cl-].[NH4+]>CO>[Si:1]([O:18][CH2:19][C:20]1[S:24][C:23]([CH2:25][OH:26])=[N:22][N:21]=1)([C:14]([CH3:15])([CH3:16])[CH3:17])([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of ethyl 5-({[tert-butyl(diphenyl)silyl]oxy}methyl)-1,3,4-thiadiazole-2-carboxylate (998 mg) in methanol (12 ml) was added sodium borohydride (177 mg), and the mixture was stirred at 0° C. for 1 hr. A saturated aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography, and the title compound (738 mg, yield 82%) was obtained as a colorless amorphous solid from a fraction eluted with ethyl acetate-hexane (2:1, volume ratio).

Workup

extractionthe mixture was extracted with ethyl acetate
dry with materialThe extract was dried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-3cf3a1b9ad7d417c95007e5385708462
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08318746B2

Reaction notes

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