Triethylborane → HCID 19746204, compound

HRID 1464825Notes

Reaction equation

HRID 1464825 reaction equation
FC(F)(F)S(O)(=O)=O.C(B(CC)CC)C.[CH2:16]([O:18][C@@H:19]([CH2:23][C:24]1[CH:25]=[CH:26][C:27]2OC(CC3N=C(C4C=CC=CC=4)OC=3C)=C[C:28]=2[CH:45]=1)[C:20]([OH:22])=[O:21])[CH3:17].C([N:49](C(C)C)CC)(C)C.[CH2:55]([O:62][C:63]1[CH:70]=[CH:69][C:66]([CH:67]=[O:68])=C[CH:64]=1)[C:56]1[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=1>ClCCl>[CH2:16]([O:18][CH:19]([CH2:23][C:24]1[CH:45]=[CH:28][C:27]([C:67](=[O:68])[CH2:66][CH2:69][C:70]2[N:49]=[C:55]([C:56]3[CH:57]=[CH:58][CH:59]=[CH:60][CH:61]=3)[O:62][C:63]=2[CH3:64])=[CH:26][CH:25]=1)[C:20]([OH:22])=[O:21])[CH3:17]

Participants

7

Reactant 5

HCID 7357TriethylboraneHCID 62406Trifluoromethanesulfonic acidHCID 78109Benzaldehyde, 4-(phenylmethoxy)-HCID 81531DiisopropylethylamineHCID 10692663HCID 10692663, compound

Product 1

HCID 19746204HCID 19746204, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
40 °C

Procedure

Trifluoromethanesulfonic acid (5.0 ml, 56 mmol) was added to a solution of triethylborane in hexanes (56 ml of a 1M solution, 56 mmol). After the bubbling stopped, the solution was heated to 40° C. for 1 hour then cooled to 0° C., a solution of (S)-4-benzyl-3-(phenoxyacetyl)oxazolidin-2-one (prepared as in Example 19) (5.0 g, 28 mmol) in dichloromethane (90 ml) was added followed by diisopropylethylamine (12.3 ml, 71 mmol) dropwise. After 30 minutes the solution was cooled to -78° C. and treated with a solution of 4-benzyloxybenzaldehyde (6.0 g, 28 mmol) in dichloromethane (80 ml). After 2 hours at -78° C., the solution was warmed to 0° C., stirred for 30 minutes and quenched with pH 7 buffer. The layers were separated, the aqueous portion was extracted with dichloromethane, the combined extracts were washed with water and brine, dried over magnesium sulfate and concentrated. The product was isolated by flash chromatography (hexanes/ethyl acetate, 1:1) as an oil (6.5 g).

Workup

  1. temperaturethen cooled to 0° C.
  2. temperatureAfter 30 minutes the solution was cooled to -78° C.
  3. temperaturethe solution was warmed to 0° C.
  4. customquenched with pH 7 buffer
  5. customThe layers were separated
  6. extractionthe aqueous portion was extracted with dichloromethane
  7. washthe combined extracts were washed with water and brine
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-658e54286dcc442d97f42d24fabd9099
Source dataset
uspto-grants-1994_04
Patent number
US05306726

Reaction notes

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