Sodium hydride → HCID 23391835, compound

HRID 990960Notes

Reaction equation

HRID 990960 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[CH2:15][CH2:14][CH2:13][C@@H:12]1[CH2:16][OH:17].[H-].[Na+]>C1COCC1>[N+:8]([C:6]1[CH:5]=[CH:4][C:3]2[N:11]3[CH2:15][CH2:14][CH2:13][C@@H:12]3[CH2:16][O:17][C:2]=2[CH:7]=1)([O-:10])=[O:9]

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 23391837HCID 23391837, compound

Product 1

HCID 23391835HCID 23391835, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A suspension of (R)-[1-(2-fluoro-4-nitrophenyl)-2-pyrrolidinyl]-methanol (2.27 g, 9.4 mmol) and NaH (60% mineral oil suspension, 0.737 g, 18.9 mmol) in 35 mL THF was heated at reflux for 1 h. The reaction was quenched with phosphate buffer, and the aqueous layer was extracted with EtOAc. The solution was filtered through Celite, and the organic layer was washed with brine, dried over MgSO4, filtered, and concentrated. Flash chromatography (3:2 EtOAc:hexanes) afforded 476 mg (22%) of (R)-2,3,3a,4-tetrahydro-7-nitro-1H-pyrrolo[2,1-c][1,4]benzoxazine, an orange solid. Data for (R)-2,3,3a,4-tetrahydro-7-nitro-1H-pyrrolo[2,1-c][1,4]benzoxazine: Rf 0.55 (3:2 hexanes:EtOAc); 1H NMR (400 MHz, CDCl3) δ 7.87 (dd, 1H, J=9,2,2,4), 7.74 (d, 1H, J=2.4), 6.44 (d, 1H, J=8.8), 4.56 (dd, 1H, J=10.3, 3.4), 3.65-3.72 (m, 1H), 3.60 (broad t, 1H, J=8.6), 3.44 (t, 1H, J=10.0), 3.36 (td, 1H, J=9.8, 7.3), 2.15-2.25 (m, 2H), 2.05-2.15 (m, 1H), 1.45-1.55 (m, 1H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1 h
  3. customThe reaction was quenched with phosphate buffer
  4. extractionthe aqueous layer was extracted with EtOAc
  5. filtrationThe solution was filtered through Celite
  6. washthe organic layer was washed with brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-5af5da80dc6849818ac79bb21c9f5af5
Source dataset
uspto-grants-2002_10
Patent number
US06462038B1

Reaction notes

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