4-Chloro-3,5-dinitrobenzotrifluoride → HCID 59293622, compound

HRID 872080Notes

Reaction equation

HRID 872080 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@@H:10]([OH:13])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CC(C)([O-])C.[K+].Cl[C:21]1[C:26]([N+:27]([O-:29])=[O:28])=[CH:25][C:24]([C:30]([F:33])([F:32])[F:31])=[CH:23][C:22]=1[N+:34]([O-:36])=[O:35]>O1CCCC1.COC(C)(C)C>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@@H:10]([O:13][C:21]2[C:22]([N+:34]([O-:36])=[O:35])=[CH:23][C:24]([C:30]([F:33])([F:31])[F:32])=[CH:25][C:26]=2[N+:27]([O-:29])=[O:28])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 98094-Chloro-3,5-dinitrobenzotrifluorideHCID 6544479tert-Butyl (3R)-3-hydroxypyrrolidine-1-carboxylateHCID 23665647Potassium tert-butoxide

Product 1

HCID 59293622HCID 59293622, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

(R)-3-hydroxypyrrolidine-1-carboxylic acid tert-butyl ester is de-protonated with potassium tert-butoxide (KOtBu) in tetrahydrofuran (THF). The resulting anion is reacted with 2-chloro-1,3-dinitro-5-trifluoromethylbenzene in tert-butyl methyl ether (MTBE)/THF. When the reaction is complete, the reaction mixture is quenched with water and partitioned with more MTBE. The organic layer is washed with brine and water and concentrated on a rotary evaporator. The solid concentrate is re-dissolved in methanol and re-precipitated with water. The resulting precipitate is filtered and dried to afford (R)-3-(2,6-dinitro-4-trifluoromethylphenoxy)pyrrolidine-1-carboxylic acid tert-butyl ester which can be used in the next step without further purification.

Workup

  1. customthe reaction mixture is quenched with water
  2. custompartitioned with more MTBE
  3. washThe organic layer is washed with brine and water
  4. concentrationconcentrated on a rotary evaporator
  5. concentrationThe solid concentrate
  6. dissolutionis re-dissolved in methanol
  7. customre-precipitated with water
  8. filtrationThe resulting precipitate is filtered
  9. customdried

Sources & evidence

ORD record
ord-ac27344b2ffc4e1b8f7604879cd69ea9
Source dataset
uspto-grants-2015_03
Patent number
US08975262B2

Reaction notes

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