Nitric Acid → HCID 89511757, compound

HRID 710596Notes

Reaction equation

HRID 710596 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1[N:10]1[CH2:14][CH2:13][CH2:12][CH2:11]1.C(O)(C(F)(F)F)=O.[N+:22]([O-])([OH:24])=[O:23]>>[N+:22]([C:6]1[CH:5]=[C:4]2[C:9](=[CH:8][CH:7]=1)[CH2:1][CH:2]([N:10]1[CH2:11][CH2:12][CH2:13][CH2:14]1)[CH2:3]2)([O-:24])=[O:23]

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 6422Trifluoroacetic acidHCID 206203Pyrrolidine, 1-(2,3-dihydro-1H-inden-2-yl)- (9CI)

Product 1

HCID 89511757HCID 89511757, compound

Conditions

Temperature
7.5 °C

Procedure

To a solution of Example 55A (8.38 g, 44.7 mmol) in TFA (320 ml, 4154 mmol) was added concentrated nitric acid (2.86 ml, 44.7 mmol) dropwise at 0° C. The mixture was stirred at 0-15° C. for 5 hours. The mixture was next concentrated then dissolved in 200 mL of ethyl acetate and the organic solution was poured into a separatory funnel and washed with saturated aqueous sodium bicarbonate (2×150 mL) and saturated aqueous brine (1×100 mL), dried over magnesium sulfate, filtered and concentrated. The crude was recrystallized in ethyl acetate/hexane mixture to give the title compound. MS (ESI) m/z 233.1 (M+H)+.

Workup

  1. concentrationThe mixture was next concentrated
  2. dissolutionthen dissolved in 200 mL of ethyl acetate
  3. additionthe organic solution was poured into a separatory funnel
  4. washwashed with saturated aqueous sodium bicarbonate (2×150 mL) and saturated aqueous brine (1×100 mL)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude was recrystallized in ethyl acetate/hexane mixture

Sources & evidence

ORD record
ord-a2eeec9e5521495a9a6b899f609f75a9
Source dataset
uspto-grants-2015_11
Patent number
US09181239B2

Reaction notes

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