Imidazole → (4aR,5S,8aS)-5-(tert-Butyl-dimethyl-silanyloxy)-8a-methyl-octahydro-naphtalen-1-one

HRID 1859002

Reaction equation

[OH:1][C@H:2]1[CH2:11][CH2:10][CH2:9][C@@:8]2([CH3:12])[C@H:3]1[CH2:4][CH2:5][CH2:6][C:7]2=[O:13].C([Si](Cl)(C)C)CCC.N1C=CN=C1.[Si:27](Cl)([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28]>CN(C)C=O>[C:30]([Si:27]([CH3:29])([CH3:28])[O:1][C@H:2]1[CH2:11][CH2:10][CH2:9][C@@:8]2([CH3:12])[C@H:3]1[CH2:4][CH2:5][CH2:6][C:7]2=[O:13])([CH3:33])([CH3:32])[CH3:31]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 2.3 g (12.6 mMol) of (4aR,5S,8aS)-5-hydroxy-8a-methyl-octahydro-naphtalen-1-one in 63 ml of dimethylformamide are added under stirring and argon atmosphere 3.74 g (24.8 mMol) of tertio-butyl-dimethyl-silylchloride and 1.94 g (28.5 mMol) of imidazole. The reaction mixture is heated to 100° C. for 4 hours, then additional 3.74 g of tert-butyl-dimethylsilylchloride and 1.94 g of imidazole are added and the reaction mixture is kept overnight at 100° C. The reaction mixture is poured onto ice-water and extracted three times with diethylether. The combined organic extract is washed once with water and brine, dried over sodium sulfate and evaporated in vacuo. The residue is chromatographed over 250 g of silicagel with hexane/ethylacetate 9/1 to yield 3.17 g (85%) of low melting cristalline (4aR,5S,8aS)-5-(tert-butyl-dimethyl-silanyloxy)-8a-methyl-octahydro-naphtalen-1-one.

Workup

additionThe reaction mixture is poured onto ice-water
extractionextracted three times with diethylether
extractionThe combined organic extract
washis washed once with water and brine
dry with materialdried over sodium sulfate
customevaporated in vacuo
customThe residue is chromatographed over 250 g of silicagel with hexane/ethylacetate 9/1

Sources & evidence

ORD record: ord-b4d0def3c575404bab48d32938b0fa1c
Source dataset: uspto-grants-2000_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06153605

Linked notes

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