Triethylsilane → HCID 67458539, compound

HRID 554576Notes

Reaction equation

HRID 554576 reaction equation
C([SiH](CC)CC)C.[CH2:8]([O:15][C@@H:16]1[C@@H:21]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C@H:20]([O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C@@H:19]([CH2:38][O:39][CH2:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[CH2:18][C:17]1([C:48]1[C:56]2[C:51](=[CH:52][CH:53]=[CH:54][CH:55]=2)[N:50]([CH2:57][C:58]2[CH:63]=[CH:62][C:61]([CH2:64][CH3:65])=[CH:60][CH:59]=2)[CH:49]=1)O)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(=O)([O-])O.[Na+]>C(Cl)Cl>[CH2:64]([C:61]1[CH:60]=[CH:59][C:58]([CH2:57][N:50]2[C:51]3[C:56](=[CH:55][CH:54]=[CH:53][CH:52]=3)[C:48]([C@@H:17]3[CH2:18][C@H:19]([CH2:38][O:39][CH2:40][C:41]4[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=4)[C@@H:20]([O:30][CH2:31][C:32]4[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=4)[C@H:21]([O:22][CH2:23][C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=4)[C@H:16]3[O:15][CH2:8][C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=3)=[CH:49]2)=[CH:63][CH:62]=1)[CH3:65]

Participants

5

Reactant 3

HCID 12052TriethylsilaneHCID 516892Sodium BicarbonateHCID 67459670HCID 67459670, compound

Product 1

HCID 67458539HCID 67458539, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

In a nitrogen stream, triethylsilane (0.21 mL, 1.22 mmol) was added dropwise to a solution of (2R,3S,4R,5R)-2,3,4-trisbenzyloxy-5-benzyloxymethyl-1-[1-(4-ethylbenzyl)-1H-indol-3-yl]cyclohexanol (469 mg, 0.61 mmol) in methylene chloride (6 mL) at 0° C. A boron trifluoride-diethyl ether complex (0.093 mL, 0.73 mmol) was added dropwise thereto over five minutes and the reaction mixture was stirred at 0° C. for two hours. A saturated sodium hydrogencarbonate aqueous solution was added to the reaction mixture and the resulting mixture was extracted with methylene chloride. The organic layer was washed with a saturated sodium chloride aqueous solution and dried over sodium sulfate. The residue obtained by distilling the solvent under reduced pressure was purified by silica gel column chromatography [developing solution=ethyl acetate:n-hexane (1:15)] to obtain the title compound (232 mg, 51%).

Workup

  1. additionA boron trifluoride-diethyl ether complex (0.093 mL, 0.73 mmol) was added dropwise
  2. extractionthe resulting mixture was extracted with methylene chloride
  3. washThe organic layer was washed with a saturated sodium chloride aqueous solution
  4. dry with materialdried over sodium sulfate
  5. customThe residue obtained
  6. distillationby distilling the solvent under reduced pressure
  7. customwas purified by silica gel column chromatography [developing solution=ethyl acetate:n-hexane (1:15)]

Sources & evidence

ORD record
ord-5e5484beb5db4d9eab21541ee9e3ad02
Source dataset
uspto-grants-2011_11
Patent number
US08048897B2

Reaction notes

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