Triethylsilane → HCID 67460266, compound

HRID 554568Notes

Reaction equation

HRID 554568 reaction equation
[CH2:1]([O:8][C@@H:9]1[C@@H:14]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C@H:13]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C@@H:12]([CH2:31][O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH2:11][C@@:10]1([C:41]1[CH:46]=[CH:45][C:44]([O:47][CH3:48])=[C:43]([CH2:49][C:50]2[CH:55]=[CH:54][C:53]([CH2:56][CH3:57])=[CH:52][CH:51]=2)[CH:42]=1)O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([SiH](CC)CC)C.C(=O)([O-])O.[Na+]>C(Cl)Cl>[CH2:56]([C:53]1[CH:52]=[CH:51][C:50]([CH2:49][C:43]2[CH:42]=[C:41]([C@@H:10]3[CH2:11][C@H:12]([CH2:31][O:32][CH2:33][C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)[C@@H:13]([O:23][CH2:24][C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=4)[C@H:14]([O:15][CH2:16][C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=4)[C@H:9]3[O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH:46]=[CH:45][C:44]=2[O:47][CH3:48])=[CH:55][CH:54]=1)[CH3:57]

Participants

5

Reactant 3

HCID 12052TriethylsilaneHCID 516892Sodium BicarbonateHCID 67460245HCID 67460245, compound

Product 1

HCID 67460266HCID 67460266, compoundYield 8.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-5 °C

Procedure

A solution of the (1S,2R,3S,4R,5R)-2,3,4-trisbenzyloxy-5-(benzyloxymethyl)-1-[3-(4-ethylbenzyl)-4-methoxyphenyl]cyclohexanol (124 mg, 0.16 mmol) as obtained in Example 65 in methylene chloride (2 mL) was cooled to −5° C., and triethylsilane (0.39 mL, 2.44 mmol) was added thereto. To the mixture, triofluoroacetic acid (0.12 mL, 1.6 mmol) was added and the reaction mixture was stirred at −5° C. for one hour, and then a saturated sodium hydrogen-carbonate was added thereto. The resulting mixture was extracted with methylene chloride and the organic layer was washed with a saturated sodium chloride aqueous solution and then dried over sodium sulfate. The solvent was distilled under reduced pressure and the obtained residue was purified by silica gel column chromatography [developing solution=ethyl acetate:n-hexane (1:9)] to obtain the title compound (10 mg, 8%).

Workup

  1. extractionThe resulting mixture was extracted with methylene chloride
  2. washthe organic layer was washed with a saturated sodium chloride aqueous solution
  3. dry with materialdried over sodium sulfate
  4. distillationThe solvent was distilled under reduced pressure
  5. customthe obtained residue was purified by silica gel column chromatography [developing solution=ethyl acetate:n-hexane (1:9)]

Sources & evidence

ORD record
ord-a0464a88f5ec4f33aae60c30a2fe97e0
Source dataset
uspto-grants-2011_11
Patent number
US08048897B2

Reaction notes

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