Potassium Carbonate → HCID 23391837, compound

HRID 990959Notes

Reaction equation

HRID 990959 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:6][C:7]=1F.[NH:12]1[CH2:16][CH2:15][CH2:14][C@@H:13]1[CH2:17][OH:18].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:6][C:7]=1[N:12]1[CH2:16][CH2:15][CH2:14][C@@H:13]1[CH2:17][OH:18]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1230531,2-Difluoro-4-nitrobenzeneHCID 2724541Prolinol, (R)-

Product 1

HCID 23391837HCID 23391837, compoundYield 96.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

A suspension of 3,4-difluoronitrobenzene (1.57 g, 9.8 mmol), (R)-2-pyrrolidinemethanol (1.0 g, 9.8 mmol) and K2CO3 (1.36 g, 9.8 mmol) in 30 mL DMF was heated at 75° C. for 20 h, whereupon the mixture was partitioned between water (100 mL) and EtOAc (100 mL). The aqueous layer was extracted with EtOAc (100 mL), and the combined organic layers washed with brine, dried over Na2SO4, filtered, and concentrated. Flash chromatography (19:1 CH2Cl2:MeOH) afforded 2.27 g (96%) of (R)-[l-(2-fluoro-4-nitrophenyl)-2-pyrrolidinyl]-methanol, an orange solid. Data for (R)-[1-(2-fluoro-4-nitrophenyl)-2-pyrrolidinyl]-methanol: Rf 0.17 (7:3 hexanes:EtOAc); 1H NMR (400 MHz, CDCl3) δ 7.94 (dd, 1H, J=9.1, 2.6), 7.89 (dd, 1H, J=14.4, 2.6), 6.68 (t, 1H, J=9.0), 4.25-4.32 (m, 1H), 3.60-3.75 (m, 3H), 3.40-3.50 (m, 1H), 1.95-2.15 (m, 4H), 1.43 (t, 1H, J=5.8).

Workup

  1. customwas partitioned between water (100 mL) and EtOAc (100 mL)
  2. extractionThe aqueous layer was extracted with EtOAc (100 mL)
  3. washthe combined organic layers washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b9c94db32ae541069ff2c790b0f64a4e
Source dataset
uspto-grants-2002_10
Patent number
US06462038B1

Reaction notes

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