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Imidazole → tert-Butyl 1-vinyl-2-(tert-butyldimethylsilyloxy)-8-azaspiro[4.5]decane-8-carboxylate

HRID 8762
Notes
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Reaction equation

HRID 8762 reaction equation
[CH:1]([CH:3]1[C:7]2([CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8]2)[CH2:6][CH2:5][CH:4]1[OH:20])=[CH2:2].N1C=CN=C1.[Si:26](Cl)([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:28])[CH3:27]>CN(C=O)C.CCOCC.C(=O)(O)[O-].[Na+]>[CH:1]([CH:3]1[C:7]2([CH2:8][CH2:9][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:11][CH2:12]2)[CH2:6][CH2:5][CH:4]1[O:20][Si:26]([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:28])[CH3:27])=[CH2:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 21983968tert-Butyl 1-vinyl-2-hydroxy-8-azaspiro[4.5]decane-8-carboxylate

Product 1

HCID 21983989tert-Butyl 1-vinyl-2-(tert-butyldimethylsilyloxy)-8-azaspiro[4.5]decane-8-carboxylateYield 86.2%

Reagents, catalysts & solvents 3

HCID 3283
Diethyl Ether
Solvent
HCID 6228DimethylformamideSolvent
HCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of tert-butyl 1-vinyl-2-hydroxy-8-azaspiro[4.5]decane-8-carboxylate (0.462 g, 1.64 mmoL) from Step A in DMF (8 mL) was added imidazole (0.335 mg, 4.92 mmol) and then tert-butyldimethylsilyl chloride (0.370 g, 2.4 mmol). The reaction was stirred at room temperature for 20 h and then diluted with ether and sodium bicarbonate solution. The mixture was extracted twice with ether. The combined ether layers were washed with brine, dried over sodium sulfate, filtered, and concentrated. The residue was purified by flash chromatography eluting with 5% ethyl acetate in hexanes to afford the title compound (0.56 g) as a mixture of isomers.

Workup

  1. extractionThe mixture was extracted twice with ether
  2. washThe combined ether layers were washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography
  7. washeluting with 5% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-9ec86a96bfa746418eba080ec0d772d5
Source dataset
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07091211B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes