Phosphate → HCID 18416184, compound

HRID 990958Notes

Reaction equation

HRID 990958 reaction equation
F[C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[N:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH:12]1[CH2:17][OH:18].[H-].[Na+].P([O-])([O-])([O-])=O>C1COCC1>[N+:8]([C:6]1[CH:5]=[CH:4][C:3]2[N:11]3[CH2:16][CH2:15][CH2:14][CH2:13][CH:12]3[CH2:17][O:18][C:2]=2[CH:7]=1)([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 1061PhosphateHCID 24758Sodium hydrideHCID 18416121HCID 18416121, compound

Product 1

HCID 18416184HCID 18416184, compoundYield 76.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A suspension of (+)-[I-(2-fluoro-4-nitrophenyl)-2-piperidinyl]-methanol (0.586 g, 2.30 mmol) and sodium hydride (60% mineral oil suspension, 0.101 g, 2.54 mmol) in 10 mL THF was heated at reflux for 16 h. The mixture was neutralized with phosphate buffer (pH 7), and the resultant solution was extracted twice with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated. Flash chromatography (7:3 hexanes:EtOAc) afforded 0.410 g (76%) of (±)-3-nitro-6,6a,7,8,9, 10-hexahydropyrido[2,1-c][1,4]benzoxazine, a yellow-orange solid. Data for (±)-3-nitro-6,6a,7,8,9,10-hexahydropyrido[2,1-c][1,4]benzoxazine: Rf O. 71 (2:3, EtOAc:hexanes) 1H NMR (400 MHz, CDCl3) δ 7.78 (dd, 1H, J=9.3, 2.9), 7.64 (d, 1H, J=2.9), 6.75 (d, 1H, J=9.3), 4.23 (dd, 1H, J=10.7, 2.9), 3.96 (dd, 1H, J=10.7, 7.8), 3.93 (m, 1H), 3,22-3.17 (m, 1H), 2.78 (td, 1H, J=12.8, 3.0), 1.95-1.92 (m, 1H), 1.88-1.84 (m, 1H), 1.75-1.71 (m, 1H), 1.66-1.60 (m, 1H), 1.58-1.48 (m, 1H), 1.35-1.27 (m, 1H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 16 h
  3. extractionthe resultant solution was extracted twice with EtOAc
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-0549a4a31d3543f58afaac23c6b57649
Source dataset
uspto-grants-2002_10
Patent number
US06462038B1

Reaction notes

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