Sodium borohydride → 4-(3,5-Bis(trifluoromethyl)phenyl)pyrrolidin-2-one

HRID 1486990Notes

Reaction equation

HRID 1486990 reaction equation
[F:1][C:2]([F:23])([F:22])[C:3]1[CH:4]=[C:5]([CH:13]([C:20]#[N:21])[CH2:14][C:15]([O:17]CC)=O)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[BH4-].[Na+]>CO.O.O.O.O.O.O.Cl[Co]Cl>[F:23][C:2]([F:1])([F:22])[C:3]1[CH:4]=[C:5]([CH:13]2[CH2:20][NH:21][C:15](=[O:17])[CH2:14]2)[CH:6]=[C:7]([C:9]([F:11])([F:12])[F:10])[CH:8]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 86658342Ethyl 3-(3,5-bis(trifluoromethyl)phenyl)-3-cyanopropanoate

Product 1

HCID 816553704-(3,5-Bis(trifluoromethyl)phenyl)pyrrolidin-2-oneYield 47.61%

Reagents, catalysts & solvents 2

HCID 517166Dichlorocobalt hexahydrateCatalystHCID 887MethanolSolvent

Conditions

Temperature
20 °C

Procedure

Ethyl 3-(3,5-bis(trifluoromethyl)phenyl)-3-cyanopropanoate (1.2 g, 1.0 eq.) was dissolved in MeOH (48 mL). Dichlorocobalt hexahydrate (1.68 g, 2.0 eq.) was added and the reaction mixture was cooled to 20° C. NaBH4 (1.98 g, 15 eq.) was added portion wise by maintaining temperature below 30° C. After completion of addition, this reaction mixture was stirred for 18 h at 25° C. The reaction mixture was concentrated under reduced pressure and the residue was partitioned between ethyl acetate (25 mL) and water (25 mL). The reaction mixture was filtered through Celite™ and the organic layer was separated, dried over Na2SO4, filtered, and concentrated under reduced pressure to afford 0.65 g of crude product, which after trituration with petroleum ether gave 0.5 g of 4-(3,5-bis(trifluoromethyl)phenyl)pyrrolidin-2-one (Yield 47.61%).

Workup

  1. temperatureby maintaining temperature below 30° C
  2. additionAfter completion of addition
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customthe residue was partitioned between ethyl acetate (25 mL) and water (25 mL)
  5. filtrationThe reaction mixture was filtered through Celite™
  6. customthe organic layer was separated
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customto afford 0.65 g of crude product, which after trituration with petroleum ether

Sources & evidence

ORD record
ord-a940cfee0d2346718d3ea149e972dce7
Source dataset
uspto-grants-2016_08
Patent number
US09428490B2

Reaction notes

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