Water → HCID 58404604, compound

HRID 1850094Notes

Reaction equation

HRID 1850094 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]([N:5]1[CH2:9][CH2:8][CH:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[O:16][CH3:17])[CH2:6]1)=[O:4].[Na+].[Br-:21].O.OOS([O-])=O.[K+]>CC(C)=O>[Br:21][C:14]1[CH:13]=[CH:12][C:11]([O:16][CH3:17])=[C:10]([CH:7]2[CH2:8][CH2:9][N:5]([C:3](=[O:4])[C:2]([F:1])([F:18])[F:19])[CH2:6]2)[CH:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 253881Sodium BromideHCID 23707502Potassium hydroxy sulfiteHCID 584046022,2,2-Trifluoro-1-[3-(2-methoxyphenyl)pyrrolidin-1-yl]ethan-1-one

Product 1

HCID 58404604HCID 58404604, compoundYield 111.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To the title compound of Step A (2.75 g, 10.1 mmol) and NaBr (4.2 g, 41 mmol) in acetone (50 mL)/H2O (50 mL) at 0° C. was added Oxone (6.2 g, 10.1 mmol) portionwise over 1 h. After 3 h, the ice bath was removed and the reaction allowed to warm to rt. Then 5 wt % Na2S2O5 (aq.) was added and the mixture extracted with EtOAc (2×). The combined organics were washed with brine and dried to give 3.95 g (>98%) of the title compound. 1H NMR (CDCl3): 7.35 (dd, J=8.7, 3.8, 2.5 Hz, 1H), 7.25 (dd, J=5.5, 2.7 Hz, 1H), 6.77 (dd, J=8.7, 4.5 Hz, 1H), 4.13-4.06 (m, 1H), 3.94-3.82 (m, 4H), 3.75-3.57 (m, 2H), 3.51-3.41 (m, 1H), 2.37-2.05 (m, 2H).

Workup

  1. customthe ice bath was removed
  2. additionThen 5 wt % Na2S2O5 (aq.) was added
  3. extractionthe mixture extracted with EtOAc (2×)
  4. washThe combined organics were washed with brine
  5. customdried

Sources & evidence

ORD record
ord-25c417765ea741a9bb23408e421f690a
Source dataset
uspto-grants-2015_02
Patent number
US08957059B2

Reaction notes

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