Imidazole → HCID 68440918, compound

HRID 2246932Notes

Reaction equation

HRID 2246932 reaction equation
[OH:1][CH2:2][C@H:3]1[N:8]([S:9]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)(=[O:11])=[O:10])[CH2:7][C@H:6]([OH:19])[C@@H:5]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)[CH2:4]1.N1C=CN=C1.[CH:33]([Si:36]([CH:41]([CH3:43])[CH3:42])([CH:38]([CH3:40])[CH3:39])Cl)([CH3:35])[CH3:34]>CN(C)C=O.Cl>[CH3:27][O:26][C:23]1[CH:22]=[CH:21][C:20]([C@H:5]2[CH2:4][C@@H:3]([CH2:2][O:1][Si:36]([CH:41]([CH3:43])[CH3:42])([CH:38]([CH3:40])[CH3:39])[CH:33]([CH3:35])[CH3:34])[N:8]([S:9]([C:12]3[CH:13]=[CH:14][C:15]([CH3:18])=[CH:16][CH:17]=3)(=[O:10])=[O:11])[CH2:7][C@@H:6]2[OH:19])=[CH:25][CH:24]=1

Participants

6

Reactant 3

HCID 795ImidazoleHCID 139400Triisopropylsilyl chlorideHCID 66886100HCID 66886100, compound

Product 1

HCID 68440918HCID 68440918, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 19.3 g of (3R,4R,6S)-6-hydroxymethyl-4-(4-methoxy-phenyl)-1-(toluene-4-sulfonyl)-piperidin-3-ol in 400 ml of N,N-dimethylformamide is added 10.9 g of imidazole and 6.79 g of triisopropylchlorosilane at room temperature. The reaction mixture is stirred overnight, diluted with 1N hydrochloric acid and extracted with tert-butyl methyl ether. The organic phases are combined, dried over sodium sulfate and concentrated under reduced pressure. The crude product is purified by flash chromatography (SiO2 60 F) to afford the title compound as a light yellow oil. Rf=0.60 (EtOAc-heptane 1:1); Rt=6.39.

Workup

  1. extractionextracted with tert-butyl methyl ether
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe crude product is purified by flash chromatography (SiO2 60 F)

Sources & evidence

ORD record
ord-34c35b94cd71465091246475924b1243
Source dataset
uspto-grants-2010_03
Patent number
US07687495B2

Reaction notes

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