Sodium Chloride → 3-[(5S)-5-(4-fluorophenyl)-5-hydroxy-1-oxopentyl]-4-phenyl-2-oxazolidinone

HRID 1831851Notes

Reaction equation

HRID 1831851 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:26])[CH2:9][CH2:10][CH2:11][C:12]([N:14]2[CH:18]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:17][O:16][C:15]2=[O:25])=[O:13])=[CH:4][CH:3]=1.B(Cl)([C@H]1[C@H](C)[C@@H]2C(C)(C)[C@@H](C2)C1)[C@H]1[C@H](C)[C@@H]2C(C)(C)[C@@H](C2)C1.[Cl-].[Na+]>C1(C)C=CC=CC=1.CCCCCCC>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([OH:26])[CH2:9][CH2:10][CH2:11][C:12]([N:14]2[CH:18]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH2:17][O:16][C:15]2=[O:25])=[O:13])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 5234Sodium ChlorideHCID 11131038Chlorobis((1R,2S,3R,5R)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-yl)boraneHCID 220526851-(4-Fluorophenyl)-5-(2-oxo-4-phenyl-3-oxazolidinyl)-1,5-pentanedione

Product 1

HCID 672605973-[(5S)-5-(4-fluorophenyl)-5-hydroxy-1-oxopentyl]-4-phenyl-2-oxazolidinoneYield 96%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 8900HeptaneSolvent

Procedure

3-[5-(4-fluorophenyl)-1,5-dioxopentyl]-4-phenyl-2-oxazolidinone (100 gm) is dissolved in toluene (750 ml), the mixture of (−)-β-chlorodiisopinocampheylborane ((−)-DIP chloride) in heptane (545 ml, 1.5M) and toluene (750 ml) is added at 0° C. to 5° C. for 1 hour. The reaction mixture is stirred for 15 hours at 25° C. to 30° C. and 340 ml of 10% sodium chloride is then added at the same temperature. The layers are separated and the organic layer is washed with 5% sodium bicarbonate (300 ml), 1N sulfuric acid (300 ml), and 10% sodium chloride (300 ml). Then the organic layer is dried on sodium sulfate to give 3-[(5S)-5-(4-fluorophenyl)-5-hydroxy-1-oxopentyl]-4-phenyl-2-oxazolidinone in 96% yield.

Workup

  1. customThe layers are separated
  2. washthe organic layer is washed with 5% sodium bicarbonate (300 ml), 1N sulfuric acid (300 ml), and 10% sodium chloride (300 ml)
  3. customThen the organic layer is dried on sodium sulfate

Sources & evidence

ORD record
ord-3deab79aceb04f6b8fc648647c9c27e7
Source dataset
uspto-grants-2006_06
Patent number
US07067675B2

Reaction notes

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