Triethylsilane → HCID 16658948, compound

HRID 1350176Notes

Reaction equation

HRID 1350176 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[N:11]1[C@H:15]([CH2:16][CH:17]([CH3:19])[CH3:18])[CH2:14][O:13][CH:12]1[C:20]([F:23])([F:22])[F:21].[SiH](CC)(CC)CC>C(Cl)(Cl)Cl.O>[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[N:11]([CH2:12][C:20]([F:23])([F:22])[F:21])[C@H:15]([CH2:16][CH:17]([CH3:18])[CH3:19])[CH2:14][OH:13]

Participants

5

Reactant 2

HCID 12052TriethylsilaneHCID 16658946HCID 16658946, compound

Product 1

HCID 16658948HCID 16658948, compoundYield 44%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

To a solution of (4R)-3-(2-fluoro-4-nitrophenyl)-4-isobutyl-2-trifluoromethyloxazolidine (4.8 g, 14.3 mmol) and Et3SiH (21.6 g, 186 mmol) in 60 mL chloroform was added BF3OEt2 (14.2, 60 mmol, added in portions) The reaction was heated at reflux for 1 d After cooling, the reaction was poured in water (200 mL) and extracted with chloroform (3 ×150 mL). The organic layers were combined, washed sequentially with water (200 mL) and brine (200 mL), dried (MgSO4), filtered, and concentrated under reduced pressure to a brown oil. Flash chromatography (gradient elution, hexanes:ethyl acetate 95:5 to 3:1) afforded 2.1 g (44%) of (2R)-2-[2-fluoro-4-nitro(2,2,2-trifluoroethyl)anilino]-4-methyl-1-pentanol, an orange oil. Data for (2R)-2-[2-fluoro-4-nitro(2,2,2-trifluoroethyl)anilino]-4-methyl-1-pentanol: Rf0.8 (3:1 hexanes:EtOAc); 1H NMR (400 MHz, CDCl3) δ 7.98 (dd, 1H, J=9.3, 2.4), 7.94 (dd, 1H, J=12.9, 2.5), 7.40 (dd, 1H, J=8.7, 8.7), 4.21–4.10 (m, 1H), 3.89–3.78 (m, 1H), 3.79–3.65 (m, 3H), 1.96–1.89 (m, 1H), 1.67–1.54 (m, 1H), 1.55–1.44 (m, 1H), 1.32–1.22 (m, 1H), 0.91 (d, 3H, J=6.6), 0.77 (d, 3H, J=6.6).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1 d
  3. temperatureAfter cooling
  4. extractionextracted with chloroform (3 ×150 mL)
  5. washwashed sequentially with water (200 mL) and brine (200 mL)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure to a brown oil
  9. washFlash chromatography (gradient elution, hexanes:ethyl acetate 95:5 to 3:1)

Sources & evidence

ORD record
ord-2d44ce6aa88347c9958cd875d3af0de2
Source dataset
uspto-grants-2007_05
Patent number
US07214690B2

Reaction notes

Loading…