Imidazole → HCID 11218790, compound

HRID 1180790Notes

Reaction equation

HRID 1180790 reaction equation
C([O:8][CH2:9][CH2:10][C:11]1([CH2:15][OH:16])[CH2:14][CH2:13][CH2:12]1)C1C=CC=CC=1.[Si:17](Cl)([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18].N1C=CN=C1.[Cl-].[NH4+]>ClCCl>[Si:17]([O:16][CH2:15][C:11]1([CH2:10][CH2:9][OH:8])[CH2:12][CH2:13][CH2:14]1)([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 25517Ammonium ChlorideHCID 28928tert-Butyldimethylsilyl chlorideHCID 11183614HCID 11183614, compound

Product 1

HCID 11218790HCID 11218790, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1.6 g (7.27 mmol) of {1-[2-(benzyloxy)ethyl]cyclobutyl}methanol in 16 mL of dichloromethane was added 1.20 g (7.99 mmol) of t-butyldimethylsilyl chloride and 0.98 g (14.54 mmol) of imidazole and the contents stirred for 16 h. Saturated ammonium chloride was added and the layers separated. The organic layer was dried with magnesium sulfate and concentrated under vacuum. To the crude silyl alcohol was added 20 mL of methanol and 0.24 g of 10 wt % palladium on carbon. The reaction was stirred under an atmosphere of hydrogen for 16 h. The contents were filtered and the filtrate was concentrated under vacuum to afford 1.71 g (97%) of 2-[1-({[tert-butyl(dimethyl)silyl]oxy}methyl)cyclobutyl]ethanol as a colorless oil. 1H NMR (300 MHz, CDCl3) δ 3.57 (s, 2H), 3.55 (t, J=6 Hz, 2H), 1.87-1.59 (m, 8H), 0.87 (2, 9H), 0.05 (s, 6H).

Workup

  1. customthe layers separated
  2. dry with materialThe organic layer was dried with magnesium sulfate
  3. concentrationconcentrated under vacuum
  4. additionTo the crude silyl alcohol was added 20 mL of methanol and 0.24 g of 10 wt % palladium on carbon
  5. stirringThe reaction was stirred under an atmosphere of hydrogen for 16 h
  6. filtrationThe contents were filtered
  7. concentrationthe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-84e0ca64afdf42f8aa0a09bebdab4f32
Source dataset
uspto-grants-2007_10
Patent number
US07282512B2

Reaction notes

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