Sodium Acetate → HCID 68756521, compound

HRID 473822Notes

Reaction equation

HRID 473822 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[CH2:13][C@H:12]([O:14]S(C)(=O)=O)[CH2:11][CH2:10][N:9]2[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[CH:4][CH:3]=1.[C:26]([O-])(=[O:28])[CH3:27].[Na+]>CS(C)=O.C(OCC)(=O)C>[C:26]([O:14][C@@H:12]1[CH2:11][CH2:10][N:9]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C@@H:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[CH2:13]1)(=[O:28])[CH3:27]

Participants

5

Reactant 2

HCID 517045Sodium AcetateHCID 86672010HCID 86672010, compound

Product 1

HCID 68756521HCID 68756521, compoundYield 55.6%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of (±)-(2S,4R)-tert-butyl 2-(4-fluorophenyl)-4-(methylsulfonyloxy)piperidine-1-carboxylate (0.30 g, 0.80 mmol) and sodium acetate (0.33 g, 4.0 mmol) in dimethylsulfoxide (15 mL) was heated to 90° C. for 2.5 hours. After cooling, the reaction mixture was diluted with ethyl acetate (40 mL), and washed with water (25 mL) and brine (25 mL). The organic layer was dried over anhydrous sodium sulfate then filtered and concentrated. The residue was purified by silica gel column chromatography (ethyl acetate:hexanes 1:10) to give (±)-(2R,4R)-tert-butyl 4-acetoxy-2-(4-fluorophenyl)piperidine-1-carboxylate (150 mg, 49% yield). 1H NMR (400 MHz, d6-DMSO): 7.24 (m, 4H), 5.14 (br s, 1H), 4.63 (m, 1H), 4.00 (br d, 1H), 2.72 (m, 1H), 2.56 (br d, 1H), 1.88 (s, 3H), 1.84 (br d 1H), 1.78 (m, 1H), 1.44 (m, 1H), 1.39 (s, 9H).

Workup

  1. temperatureAfter cooling
  2. washwashed with water (25 mL) and brine (25 mL)
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. filtrationthen filtered
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexanes 1:10)

Sources & evidence

ORD record
ord-c2037fd7e3e94fc384d7aac6ee2e4a70
Source dataset
uspto-grants-2014_01
Patent number
US08637499B2

Reaction notes

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