Potassium Bromide → HCID 66580194, compound

HRID 2092682Notes

Reaction equation

HRID 2092682 reaction equation
[OH:1][CH:2]1[CH2:25][CH2:24][C:5]2([C:9](=[O:10])[N:8]([C:11]3[CH:16]=[CH:15][C:14]([O:17][C@@H:18]([CH3:23])[C:19]([F:22])([F:21])[F:20])=[CH:13][CH:12]=3)[CH2:7][CH2:6]2)[CH2:4][CH2:3]1.CC1(C)N([O])C(C)(C)CCC1.[Br-].[K+].Cl[O-].[Na+].C(=O)(O)[O-].[Na+]>C(Cl)Cl.O.CC1(C)N([O])C(C)(C)CCC1>[F:22][C:19]([F:20])([F:21])[C@H:18]([CH3:23])[O:17][C:14]1[CH:15]=[CH:16][C:11]([N:8]2[CH2:7][CH2:6][C:5]3([CH2:4][CH2:3][C:2](=[O:1])[CH2:25][CH2:24]3)[C:9]2=[O:10])=[CH:12][CH:13]=1

Participants

9

Reactant 5

HCID 253877Potassium BromideHCID 516892Sodium BicarbonateHCID 2724126TempoHCID 23665760Sodium Hypochlorite2×HCID 66580295HCID 66580295, compound

Product 1

HCID 66580194HCID 66580194, compoundYield 95%

Reagents, catalysts & solvents 3

HCID 2724126TempoCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 8-hydroxy-2-[4-((S)-2,2,2-trifluoro-1-methyl-ethoxy)-phenyl]-2-aza-spiro[4.5]decan-1-one (5.79 g) and 2,2,6,6-tetramethylpiperidine-1-oxyl radical (TEMPO) (506 mg) in CH2Cl2 (85 mL) was added a solution of potassium bromide (482 mg) in water (16 mL). Then, sodiumhypochlorite (13%, 42.5 mL) was added dropwise over a period of 10 minutes, followed by sodium bicarbonate (NaHCO3) (4.08 g). The mixture was stirred for 1.5 hours at RT. TLC showed a remainder of starting material. More TEMPO (125 mg) and sodiumhypochlorite solution (10 mL) were added and the mixture was stirred for an additional 2 hours at RT. The reaction was poured into ice/water and was extracted three times with CH2Cl2. The combined organic layers were washed with brine, dried over Na2SO4 and filtered. The solvent was evaporated and the crude material was purified by flash chromatography (silica gel, gradient of heptane in ethyl acetate) to provide the title compound as a light brown solid (5.47 g). MS (m/e): 356.1 (MH+).

Workup

  1. stirringthe mixture was stirred for an additional 2 hours at RT
  2. extractionwas extracted three times with CH2Cl2
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customThe solvent was evaporated
  7. customthe crude material was purified by flash chromatography (silica gel, gradient of heptane in ethyl acetate)

Sources & evidence

ORD record
ord-a4697f2c8ebe4dd6b531e3a12c1f5a5c
Source dataset
uspto-grants-2013_05
Patent number
US08440710B2

Reaction notes

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