Triethylsilane → HCID 67311454, compound

HRID 2090064Notes

Reaction equation

HRID 2090064 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:27]2[CH:28]=[N:29][C:30]3[C:35]([CH:36]=2)=[CH:34][CH:33]=[C:32]([C:37]([F:40])([F:39])[F:38])[CH:31]=3)(O)[C@@H:9]([C:13]2[CH:25]=[CH:24][C:16]([C:17]([O:19]C(C)(C)C)=[O:18])=[CH:15][CH:14]=2)[CH2:10][CH2:11][CH3:12])=[CH:4][CH:3]=1.C([SiH](CC)CC)C>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:27]2[CH:28]=[N:29][C:30]3[C:35]([CH:36]=2)=[CH:34][CH:33]=[C:32]([C:37]([F:40])([F:38])[F:39])[CH:31]=3)[C@@H:9]([C:13]2[CH:14]=[CH:15][C:16]([C:17]([OH:19])=[O:18])=[CH:24][CH:25]=2)[CH2:10][CH2:11][CH3:12])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 68300407HCID 68300407, compound

Product 1

HCID 67311454HCID 67311454, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

The product of step A (98 mg, 0.173 mmol) was dissolved in CH2Cl2 (15 mL) and triethylsilane (0.28 ml, 1.72 mmol) was added. The solution was cooled to −78° C., then BF3 gas was slowly bubbled through the solution until it was saturated (less than one minute, at the time fuming BF3 was observed from a small needle venting from the flask). The mixture was allowed to warm gradually to −20° C. When all starting material was consumed by LC/MS analysis, saturated NaHCO3 (aq) was added and the mixture was allowed to warm to room temperature. The mixture was extracted twice with EtOAc. The combined organic extracts were washed with water, dried over MgSO4, filtered, then concentrated. This afforded a mixture of diastereomers of the title compound, which was used in the next step without purification: LC1 2.39 min, (M+H) 498,

Workup

  1. customBF3 gas was slowly bubbled through the solution until it
  2. customless than one minute
  3. temperatureto warm gradually to −20° C
  4. customWhen all starting material was consumed by LC/MS analysis, saturated NaHCO3 (aq)
  5. additionwas added
  6. temperatureto warm to room temperature
  7. extractionThe mixture was extracted twice with EtOAc
  8. washThe combined organic extracts were washed with water
  9. dry with materialdried over MgSO4
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customThis afforded

Sources & evidence

ORD record
ord-de55860aef684ab98b689b72a06ca4ae
Source dataset
uspto-grants-2013_05
Patent number
US08436015B2

Reaction notes

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