Imidazole → HCID 178455354, compound

HRID 1968965Notes

Reaction equation

[Si:1](Cl)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[OH:9][C@H:10]1[CH2:15][CH2:14][C@H:13]([N:16]2[C:20](=[O:21])[C:19]3=[CH:22][CH:23]=[CH:24][CH:25]=[C:18]3[C:17]2=[O:26])[CH2:12][CH2:11]1.N1C=CN=C1>CN(C=O)C>[Si:1]([O:9][C@H:10]1[CH2:11][CH2:12][C@H:13]([N:16]2[C:17](=[O:26])[C:18]3=[CH:25][CH:24]=[CH:23][CH:22]=[C:19]3[C:20]2=[O:21])[CH2:14][CH2:15]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 40 °C

Procedure

tert-Butyldimethylsilyl chloride (60 g; 0.39 mol) was added in portions to a mixture of trans N-(4-hydroxycyclohexyl)phthalimide (D62, 95 g; 0.39 mol), imidazole (55 g; 0.78 mol), and DMF (200 mL) at 20-30° C. (internal, ice cooling). After stirring for 3 h more at 40° C. the mixture was partitioned between water/hexane. Drying and evaporation of the organic layer gave the title compound (92 g) crystallised from pentane.

Workup

customwas partitioned between water/hexane
customDrying
customevaporation of the organic layer

Sources & evidence

ORD record: ord-cbaef918a19647d0ad590fc015dc84a0
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08426443B2

Reaction notes

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