Imidazole → ((1R,2S,4R,5S)-5-(Benzyloxy)bicyclo[2.2.1]heptan-2-yloxy)(tert-butyl)diphenylsilane

HRID 46152Notes

Reaction equation

HRID 46152 reaction equation
[CH2:1]([O:8][C@H:9]1[CH2:14][C@H:13]2[CH2:15][C@@H:10]1[CH2:11][C@@H:12]2[OH:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:17]([Si:21](Cl)([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([CH3:20])([CH3:19])[CH3:18].N1C=CN=C1>CN(C=O)C>[CH2:1]([O:8][C@H:9]1[CH2:14][C@H:13]2[CH2:15][C@@H:10]1[CH2:11][C@@H:12]2[O:16][Si:21]([C:17]([CH3:20])([CH3:19])[CH3:18])([C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 94078tert-ButyldiphenylchlorosilaneHCID 10036335(1R,2S,4R,5S)-5-(Benzyloxy)bicyclo[2.2.1]heptan-2-ol

Product 1

HCID 58951349((1R,2S,4R,5S)-5-(Benzyloxy)bicyclo[2.2.1]heptan-2-yloxy)(tert-butyl)diphenylsilane

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (1R,2S,4R,5S)-5-(benzyloxy)bicyclo[2.2.1]heptan-2-ol (4.20 g, 19.2 mmol) in DMF (10 mL) was added tert-butylchlorodiphenylsilane (6.00 mL, 23.1 mmol) and imidazole (3.27 g, 48.1 mmol). The resulting mixture was stirred at ambient temp. overnight. The mixture was partitioned between diethyl ether and water. The organic portion was separated, washed with brine, and concentrated in vacuo. The residue was purified by flash column chromatography (0 to 5% of EtOAc in hexanes) to give the title compound as a colorless oil.

Workup

  1. customThe mixture was partitioned between diethyl ether and water
  2. customThe organic portion was separated
  3. washwashed with brine
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash column chromatography (0 to 5% of EtOAc in hexanes)

Sources & evidence

ORD record
ord-bfe25aa8bd5c481eb73d285c65586a4a
Source dataset
uspto-grants-2013_09
Patent number
US08541592B2

Reaction notes

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