Triethylsilane → HCID 86706974, compound

HRID 1750303Notes

Reaction equation

HRID 1750303 reaction equation
FC(F)(F)S(O[Si](C)(C)C)(=O)=O.C([SiH](CC)CC)C.[CH2:20]([N:27]1[CH2:32][CH2:31][O:30][C:29]([C:34]2[O:38][N:37]=[C:36]([CH3:39])[CH:35]=2)(O)[CH2:28]1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(=O)(O)[O-].[Na+]>ClCCl>[CH2:20]([N:27]1[CH2:32][CH2:31][O:30][CH:29]([C:34]2[O:38][N:37]=[C:36]([CH3:39])[CH:35]=2)[CH2:28]1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

6

Reactant 4

HCID 12052TriethylsilaneHCID 65367Trimethylsilyl triflateHCID 516892Sodium BicarbonateHCID 86706975HCID 86706975, compound

Product 1

HCID 86706974HCID 86706974, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

Trimethylsilyl trifluoromethanesulfonate (2.9 g, 13 mmol) and triethylsilane (2.6 g, 22 mmol) were added to a solution of 4-benzyl-2-(3-methyl-1,2-oxazol-5-yl)morpholin-2-ol (C36) (1.2 g, 4.4 mmol) in dichloromethane (15 mL), and the reaction mixture was heated at 80° C. for 2 hours. The reaction mixture was then adjusted to a pH of 5 to 6 via addition of saturated aqueous sodium bicarbonate solution. After extraction with dichloromethane (3×20 mL), the combined organic layers were washed with saturated aqueous sodium chloride solution (25 mL), dried over sodium sulfate, filtered, and concentrated. Purification via silica gel chromatography (Gradient: 0% to 50% ethyl acetate in petroleum ether) afforded the product as a yellow oil. Yield: 500 mg, 1.9 mmol, 43%. LCMS m/z 258.9 [M+H+]. 1H NMR (400 MHz, CDCl3) δ 7.27-7.37 (m, 5H), 6.07 (s, 1H), 4.75 (dd, J=9.7, 2.3 Hz, 1H), 3.96 (ddd, J=11.3, 2.8, 2.4 Hz, 1H), 3.81 (ddd, J=11.3, 10.8, 2.5 Hz, 1H), 3.52-3.61 (m, 2H), 3.02 (br d, J=11.4 Hz, 1H), 2.68-2.75 (m, 1H), 2.29 (s, 3H), 2.27-2.37 (m, 2H).

Workup

  1. extractionAfter extraction with dichloromethane (3×20 mL)
  2. washthe combined organic layers were washed with saturated aqueous sodium chloride solution (25 mL)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification via silica gel chromatography (Gradient: 0% to 50% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-065d42e2757f4d9a9f2d85d0888c152e
Source dataset
uspto-grants-2015_10
Patent number
US09156845B2

Reaction notes

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