tert-Butyldimethylsilyl chloride → HCID 86682901, compound

HRID 1522877Notes

Reaction equation

HRID 1522877 reaction equation
[CH3:1][C:2]([Si:5](Cl)([CH3:7])[CH3:6])([CH3:4])[CH3:3].[CH3:9][C:10]1[N:11]=[CH:12][N:13]([C@@H:15]([CH3:18])[CH2:16][OH:17])[CH:14]=1>C(Cl)Cl>[Si:5]([O:17][CH2:16][C@@H:15]([N:13]1[CH:14]=[C:10]([CH3:9])[N:11]=[CH:12]1)[CH3:18])([C:2]([CH3:4])([CH3:3])[CH3:1])([CH3:7])[CH3:6]

Participants

4

Reactant 2

HCID 28928tert-Butyldimethylsilyl chlorideHCID 86682902HCID 86682902, compound

Product 1

HCID 86682901HCID 86682901, compoundYield 2.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a 500-mL round-bottom flask, (S)-2-(4-methyl-1H-imidazol-1-yl)propan-1-ol (12.0 g) and TEA (12 mL) were dissolved in DCM at room temperature. To this solution, TBSCl (21.3 g, 0.141 mol) was added, and the resulting mixture was stirred at room temperature overnight. The mixture was washed with H2O, the organic phase was separated, and the aqueous was extracted with DCM. The combined organic layers were washed with brine (50 mL), dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified on a silica gel column eluted with 1/30-1/9 MeOH/DCM, affording a sample (1.20 g), which was further purified by prep-HPLC, to afford the title compound (0.557 g). 1H NMR (CDCl3): δ 7.41 (d, 1H), 6.67-6.65 (m, 1H), 4.16-4.10 (m, 1H), 3.73-3.62 (m, 2H), 2.20 (d, 3H), 1.44 (d, 3H), 0.86 (s, 9H), −0.04 (s, 6H); LCMS: 255 (M+H)+.

Workup

  1. washThe mixture was washed with H2O
  2. customthe organic phase was separated
  3. extractionthe aqueous was extracted with DCM
  4. washThe combined organic layers were washed with brine (50 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified on a silica gel column
  9. washeluted with 1/30-1/9 MeOH/DCM
  10. customaffording a sample (1.20 g), which
  11. customwas further purified by prep-HPLC,

Sources & evidence

ORD record
ord-65e4a9ef830440c79f5ad9e09e99fef0
Source dataset
uspto-grants-2015_07
Patent number
US09078871B2

Reaction notes

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