Dichloromethane → HCID 67458545, compound

HRID 554560Notes

Reaction equation

HRID 554560 reaction equation
Cl[Si](C)(C)C.C([BH3-])#N.[Na+].[CH:10]1([C:13]2[CH:18]=[CH:17][C:16]([C:19]([C:21]3[S:22][C:23]([CH3:66])=[CH:24][C:25]=3[O:26][C@@H:27]3[CH2:32][C@H:31]([CH2:33][O:34][CH2:35][C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)[C@@H:30]([O:42][CH2:43][C:44]4[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=4)[C@H:29]([O:50][CH2:51][C:52]4[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=4)[C@H:28]3[O:58][CH2:59][C:60]3[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=3)=O)=[CH:15][CH:14]=2)[CH2:12][CH2:11]1.C(Cl)Cl>C(#N)C>[CH:10]1([C:13]2[CH:14]=[CH:15][C:16]([CH2:19][C:21]3[S:22][C:23]([CH3:66])=[CH:24][C:25]=3[O:26][C@@H:27]3[CH2:32][C@H:31]([CH2:33][O:34][CH2:35][C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)[C@@H:30]([O:42][CH2:43][C:44]4[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=4)[C@H:29]([O:50][CH2:51][C:52]4[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=4)[C@H:28]3[O:58][CH2:59][C:60]3[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=3)=[CH:17][CH:18]=2)[CH2:11][CH2:12]1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 6397ChlorotrimethylsilaneHCID 5003444Sodium cyanoborohydrideHCID 67460202HCID 67460202, compound

Product 1

HCID 67458545HCID 67458545, compoundYield 58.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

In a nitrogen stream, chlorotrimethylsilane (0.46 mL, 3.56 mmol) and sodium cyanoborohydride (230 mg, 3.65 mmol) were added to an solution of (4-cyclopropylphenyl)-[5-methyl-3-((1R,2S,3S,4R,5R)-2,3,4-trisbenzyloxy-5-benzyloxymethylcyclohexyloxy)thiophen-2-yl]methanone (237 mg, 0.30 mmol) in acetonitrile (5 mL) under cooling with ice and the reaction mixture was stirred at 0° C. for one hour. Methylene chloride was added thereto and the mixture was subjected to Celite filtration, and the solvent of the filtrate was distilled under reduced pressure. The obtained residue was purified by silica gel column chromatography [developing solution=ethyl acetate:n-hexane (1:10)] to obtain the title compound (135 mg, 58%).

Workup

  1. temperatureunder cooling with ice
  2. filtrationthe mixture was subjected to Celite filtration
  3. distillationthe solvent of the filtrate was distilled under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography [developing solution=ethyl acetate:n-hexane (1:10)]

Sources & evidence

ORD record
ord-7c0874327cfd4aff95eb102cc6900c0b
Source dataset
uspto-grants-2011_11
Patent number
US08048897B2

Reaction notes

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