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

HRID 1075551Notes

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].N1C=CN=C1.[C:19]([Si:23](Cl)([CH3:25])[CH3:24])([CH3:22])([CH3:21])[CH3:20]>CN(C)C=O>[C:19]([Si:23]([CH3:25])([CH3:24])[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])([CH3:22])([CH3:21])[CH3:20]

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-silychloride 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-dimethyl-silylchloride 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 silica gel with hexane/ethylacetate 9/1 to yield 3.17 g (85%) of low melting crystalline (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 silica gel with hexane/ethylacetate 9/1

Sources & evidence

ORD record: ord-6d7dc72e97864f60ab70f1b31ec35d8f
Source dataset: uspto-grants-1999_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05905074

Reaction notes

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