Imidazole → [t-Butyl(dimethyl)silyloxymethyl]-2-piperidone
Reaction equation
[Si:1](Cl)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].OC[CH:11]1[CH2:16][NH:15][C:14](=[O:17])[CH2:13][CH2:12]1.N1C=CN=C1.CN([CH:26]=[O:27])C>>[Si:1]([O:27][CH2:26][N:15]1[CH2:16][CH2:11][CH2:12][CH2:13][C:14]1=[O:17])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]Participants
Conditions
- Temperature
- 22 °C
Procedure
To a solution of 5.8 g tert-butyl(dimethyl)silyl chloride and 5.0 g of 5-hydroxymethyl-2-piperidone in 150 ml of anhydrous DMF was added 5.3 g of imidazole. After stirring for 36 hours at 22° C., the mixture was evaporated under vacuum to remove most of the DMF. Following the addition of water, the residue was extracted with three portions of ethyl acetate. The combined organic extracts were washed with water, 0.5N HCl, water and brine, dried over magnesium sulfate and evaporated. The resulting oil was chromatographed over silica gel eluting with 5% methanol in chloroform to give 4.7 g of the title compound as an oil: MS m/z 244 (M+), 186 [M+ -58(t-butyl)]; 300-MHz 1H NMR (CDCl3) δ0.05 (s, 6 H), 0.85 (s, 9 H), 1.42-1.57 (m, 1 H), 1.77-1.88 (m, 1 H), 1.89-2.03 (m, 1 H), 2.25- 2.45 (m, 2 H), 3.03 (t, J=9 Hz, 1 H), 3.30-3.41 (m, 1 H), 3.45-3.59 (m, 2 H), 5.95 (s, 1 H).
Workup
- customthe mixture was evaporated under vacuum
- customto remove most of the DMF
- additionthe addition of water
- extractionthe residue was extracted with three portions of ethyl acetate
- washThe combined organic extracts were washed with water, 0.5N HCl, water and brine
- dry with materialdried over magnesium sulfate
- customevaporated
- customThe resulting oil was chromatographed over silica gel eluting with 5% methanol in chloroform
Sources & evidence
- ORD record
- ord-09999afcdf5e4439943c9d215c2b8fc0
- Source dataset
- uspto-grants-1992_10
- Patent number
- US05159079
Reaction notes
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