Sodium Hydroxide → HCID 58218883, compound

HRID 62637Notes

Reaction equation

HRID 62637 reaction equation
[Mg].[Cl-].[Li+].[CH2:4]([N:11]1[CH2:15][CH:14](S(C2C=CC=CC=2)(=O)=O)[C:13]([C:29]2[CH:34]=[C:33]([Cl:35])[CH:32]=[C:31]([Cl:36])[CH:30]=2)([C:25]([F:28])([F:27])[F:26])[CH2:12]1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[OH-:37].[Na+]>CO.O>[CH2:4]([N:11]1[CH2:15][CH2:14][C:13]([C:29]2[CH:30]=[C:31]([Cl:36])[CH:32]=[C:33]([Cl:35])[CH:34]=2)([C:25]([F:28])([F:27])[F:26])[CH2:12]1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[CH:5]([OH:37])([CH3:10])[CH3:4]

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 433294Lithium ChlorideHCID 5462224Magnesium4×HCID 118271394HCID 118271394, compound

Product 2

HCID 3776IsopropanolYield 29%HCID 58218883HCID 58218883, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Conditions

Temperature
45 °C

Procedure

Magnesium (47.3 mg, 1.94 mmol), lithium chloride (41.2 mg, 972 μmol) and 1-benzyl-3-(3,5-dichlorophenyl)-4-(phenylsulfonyl)-3-(trifluoromethyl)pyrrolidine (500 mg, 972 μmol) were put in a flask under argon atmosphere. Methanol (5 mL) was added and the reaction was stirred for 4.5 hours and one additional hour after adding more magnesium (2 eq.). After standing over night the reaction was heated to 45° C. for seven hours adding magnesium (1 eq. each) after two and five hours. Again after standing over night magnesium was added (1 eq.) and the reaction heated to 45° C. for three hours. Water (2 mL) and methanol was added. After cooling to room temperature sodium hydroxide solution (10%) was added. The precipitate was filtered off, dissolved in ethyl acetate and methanol, washed with hydrochloric acid (10%). The organic phase was dried over sodium sulfate, filtered and the solvents evaporated. The crude 1-benzyl-3-(3,5-dichlorophenyl)-3-(trifluoromethyl)pyrrolidine (308 mg, 69% purity, 59% yield) was crystallized from iso-propanol (111 mg, 95% purity, 29% yield).

Workup

  1. waitAfter standing over night
  2. waitAgain after standing over night
  3. temperaturethe reaction heated to 45° C. for three hours
  4. additionwas added
  5. filtrationThe precipitate was filtered off
  6. dissolutiondissolved in ethyl acetate
  7. washmethanol, washed with hydrochloric acid (10%)
  8. dry with materialThe organic phase was dried over sodium sulfate
  9. filtrationfiltered
  10. customthe solvents evaporated

Sources & evidence

ORD record
ord-0e2860d41a224227acb47d29c912e7d7
Source dataset
uspto-grants-2016_09
Patent number
US09447036B2

Reaction notes

Loading…