Imidazole → Cyclohexanemethanol, 4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-, cis-

Temperature

20 °C

tert-Butyldimethylsilyl chloride (8.8 g, 58 mmol) was added to a solution of ethyl 4-hydroxycyclohexanecarboxylate (10 g, 58 mmol) and imidazole (4.3 g, 64 mmol) in DCM (300 ml), and the mixture was stirred overnight at 20° C. After washing with water (2×100 ml), the organic phase was dried (MgSO4) and evaporated to dryness. The residue was dissolved in dry THF (300 ml) and cooled to −10° C. Dibal-H (1.0 M in toluene, 174 ml, 174 mmol) was added dropwise over a period of 60 min, while the temperature was kept at −10° C. After stirring for 2 hrs the reaction was quenched by slow addition of a saturated ammonium chloride solution (30 ml). The resulting suspension was filtered, and the filtrate was concentrated in vacuo to give 13 g of the title compound as a mixture of two isomers. LC-MS (m/z): 245 (M+1).

1. washAfter washing with water (2×100 ml)
2. dry with materialthe organic phase was dried (MgSO4)
3. customevaporated to dryness
4. dissolutionThe residue was dissolved in dry THF (300 ml)
5. temperaturecooled to −10° C
6. customwas kept at −10° C
7. stirringAfter stirring for 2 hrs the reaction
8. customwas quenched by slow addition of a saturated ammonium chloride solution (30 ml)
9. filtrationThe resulting suspension was filtered
10. concentrationthe filtrate was concentrated in vacuo

ORD record

ord-e52583ab84d243fcb1b9b09489653700

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08809540B2