tert-Butyldimethylsilyl chloride → HCID 178455368, compound

HRID 2235230Notes

Reaction equation

HRID 2235230 reaction equation
[CH2:1]([O:8][C:9](=[O:18])[NH:10][C@H:11]1[CH2:16][CH2:15][C@H:14]([OH:17])[CH2:13][CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Si:19](Cl)([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20]>C1COCC1>[CH2:1]([O:8][C:9](=[O:18])[NH:10][C@H:11]1[CH2:16][CH2:15][C@H:14]([O:17][Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20])[CH2:13][CH2:12]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 28928tert-Butyldimethylsilyl chlorideHCID 178523817HCID 178523817, compound

Product 1

HCID 178455368HCID 178455368, compoundYield 98.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Combine trans-(4-hydroxy-cyclohexyl)-carbamic acid benzyl ester (16.0 g, 0.064 mol), immidazol (13.9 g, 0.10 mol), and anhydrous THF (300 mL), add tert-butyldimethylsilyl chloride (14.5 g, 0.10 mol) and stir at room temperature for 18 hours. Wash the reaction mixture with water (250 mL), saturated aqueous NaHCO3 (250 mL) and dry the organic layer over anhydrous Na2SO4. Remove the solvent and purify the residue by chromatography over silica gel (eluting with 0 to 30% EtOAc in hexane) to obtain trans-[4-(tert-butyl-dimethyl-silanyloxy)-cyclohexyl]-carbamic acid benzyl ester as clear oil (23.0 g, 98%).

Workup

  1. washWash the reaction mixture with water (250 mL), saturated aqueous NaHCO3 (250 mL)
  2. dry with materialdry the organic layer over anhydrous Na2SO4
  3. customRemove the solvent
  4. custompurify the residue by chromatography over silica gel (eluting with 0 to 30% EtOAc in hexane)

Sources & evidence

ORD record
ord-3e8e077776f845fabda2cd72c1a617ff
Source dataset
uspto-grants-2010_05
Patent number
US07713979B2

Reaction notes

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