Imidazole → 5-[t-Butyl(dimethyl)silyloxymethyl]-2-piperidone

HRID 741870Notes

Reaction equation

[Si:1](Cl)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[OH:9][CH2:10][CH:11]1[CH2:16][NH:15][C:14](=[O:17])[CH2:13][CH2:12]1.N1C=CN=C1>CN(C=O)C>[Si:1]([O:9][CH2:10][CH:11]1[CH2:16][NH:15][C:14](=[O:17])[CH2:13][CH2:12]1)([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 35 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, 6H), 0.85 (s, 9H), 1.42-1.57 (m, 1H), 1.77-1.88 (m, 1H), 1.89-2.03 (m, 1H), 2.25-2.45 (m, 2H), 3.03 (t, J=9 Hz, 1H), 3.30-3.41 (m, 1H), 3.45-3.59 (m, 2H), 5.95 (s, 1H).

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-083a121095364b9ca1b5d53d58ad22ac
Source dataset: uspto-grants-1996_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05552545

Reaction notes

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