Fluorobenzene → HCID 70505617, compound

HRID 1262614Notes

Reaction equation

HRID 1262614 reaction equation
[H-].[Na+].[CH2:3]([N:10]1[CH2:14][CH:13]([OH:15])[CH:12]([OH:16])[CH2:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.F[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CN(C)C=O>[O:15]([C@H:13]1[CH2:14][N:10]([CH2:3][C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:11][C@H:12]1[OH:16])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 10008FluorobenzeneHCID 24758Sodium hydrideHCID 536645rac-(3R,4S)-1-benzylpyrrolidine-3,4-diol

Product 1

HCID 70505617HCID 70505617, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
50 °C

Procedure

A slurry of 2.4 g. (0.1 mole) of sodium hydride (4.2 g. of 57% oil dispersion, washed with ether to remove the oil) in 30 ml. of dimethylformamide was stirred while a solution of 19.3 g. (0.1 mole) of 1-benzyl-3,4-dihydroxypyrrolidine, cis isomer, (I) in 30 ml. of dimethylformamide was added dropwise. The mixture was heated at 50° C. for 1 hr., then a solution of 19.2 g. (0.2 mole) of fluorobenzene in 30 ml. of dimethylformamide was added in one portion. The mixture was heated at 90° C. for 18 hr., then cooled and concentrated under vacuum. The residue was dissolved in benzene and washed with water. The semicrystalline residue from the concentrated organic fraction was dissolved in cyclohexane and the solution was decanted from an insoluble oil (mostly I). The cyclohexane solution was treated with charcoal to remove residual I and then crystallized as fluffy, off-white needles (m.p. 88.5°-90° d.) which weighed 1.2 g. (4.5%).

Workup

  1. washof 57% oil dispersion, washed with ether
  2. customto remove the oil) in 30 ml
  3. temperatureThe mixture was heated at 90° C. for 18 hr
  4. temperature, then cooled
  5. concentrationconcentrated under vacuum
  6. dissolutionThe residue was dissolved in benzene
  7. washwashed with water
  8. dissolutionThe semicrystalline residue from the concentrated organic fraction was dissolved in cyclohexane
  9. customthe solution was decanted from an insoluble oil (mostly I)
  10. additionThe cyclohexane solution was treated with charcoal
  11. customto remove residual I
  12. customcrystallized as fluffy, off-white needles (m.p. 88.5°-90° d.) which

Sources & evidence

ORD record
ord-04de211680c54a22ac4cfd5141ddf8b4
Source dataset
uspto-grants-1984_06
Patent number
US04452809

Reaction notes

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