Acetone → HCID 57473821, compound

HRID 576590Notes

Reaction equation

HRID 576590 reaction equation
[CH2:1]([C:4]1([CH:25]([CH3:27])[CH3:26])[CH2:8][CH2:7][N:6]([CH2:9][C:10]2[CH:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:13]=[C:12]([C:20]([F:23])([F:22])[F:21])[CH:11]=2)[C:5]1=[O:24])[CH:2]=C.CSC.CC(C)=[O:33]>>[F:21][C:20]([F:23])([F:22])[C:12]1[CH:11]=[C:10]([CH:15]=[C:14]([C:16]([F:19])([F:17])[F:18])[CH:13]=1)[CH2:9][N:6]1[CH2:7][CH2:8][C:4]([CH2:1][CH:2]=[O:33])([CH:25]([CH3:27])[CH3:26])[C:5]1=[O:24]

Participants

4

Reactant 3

HCID 180AcetoneHCID 1068Dimethyl SulfideHCID 57473820HCID 57473820, compound

Product 1

HCID 57473821HCID 57473821, compound

Procedure

A solution of 3-allyl-1-(3,5-bis(trifluoromethyl)-benzyl)-3-isopropylpyrrolidin-2-one (1.0 g, 2.54 mmol) in acetone (9 mL) was cooled to −78° C. O3 was bubbled through this solution until the color had changed from colorless to blue (30 min). At this point nitrogen gas was bubbled through the solution for 5 minutes, and dimethyl sulfide (1.88 mL, 25.4 mmol) was added. The solution was allowed to warm to room temperature over 2 h, and then concentrated in vacuo to yield impure 2-(1-(3,5-bis(trifluoromethyl)benzyl)-3-isopropyl-2-oxopyrrolidin-3-yl)acetaldehyde as a clear oil. Key non-solvent resonances in 1H-NMR (400 MHz, CDCl3) δ=9.81 (s, 1H), 8.0-7.8 (m, 3H), 5.2-5.0 (m, 1H), 4.7-4.5 (m, 1H), 3.4-3.1 (m, 2H), 2.2-1.8 (m, 5H), 1.0-0.8 (m, 6H).

Workup

  1. customO3 was bubbled through this solution until the color
  2. customcolorless to blue (30 min)
  3. customAt this point nitrogen gas was bubbled through the solution for 5 minutes
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-72f6633e7a9a4b9083f36861275363a6
Source dataset
uspto-grants-2015_05
Patent number
US09040526B2

Reaction notes

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