Selectfluor → TERT-BUTYL 3-FLUORO-4-OXOPIPERIDINE-1-CARBOXYLATE

HRID 877667Notes

Reaction equation

HRID 877667 reaction equation
C[Si](C)(C)[O:3][C:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH:5]=1.[B-](F)(F)(F)[F:20].[B-](F)(F)(F)F.C1[N+]2(CCl)CC[N+](F)(CC2)C1>C(#N)C.C(OCC)(=O)C>[F:20][CH:9]1[C:4](=[O:3])[CH2:5][CH2:6][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:8]1

Participants

5

Reactant 2

HCID 2724933SelectfluorHCID 10778540tert-Butyl 4-((trimethylsilyl)oxy)-5,6-dihydropyridine-1(2H)-carboxylate

Product 1

HCID 10560711TERT-BUTYL 3-FLUORO-4-OXOPIPERIDINE-1-CARBOXYLATEYield 62.5%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of tert-butyl 4-(trimethylsilyloxy)-5,6-dihydropyridine-1(2H)-carboxylate (0.5 g, 1.84 mmol) in dry acetonitrile (5.0 mL) was added SelectFluor (0.654 g, 1.84 mmol), and the reaction mixture was stirred for 75 minutes. At this time, the reaction mixture was diluted with ethyl acetate (50 mL) and washed with brine (50 mL), dried over anhyd. Na2SO4 and concentrated under vacuum to give the title compound (0.25 g, 62%) which was used as obtained for the next transformation. LCMS (Condition D): m/z 218.2 +ve with retention time=1.51 min. 1H-NMR (400 MHz, CDCl3) δ ppm: 4.30-4.42 (m, 1H), 3.72-3.84 (m, 1H), 3.42-3.58 (m, 3H), 1.93-1.97 (m, 1H), 1.70-1.74 (m, 1H), 1.46 (s, 9H). 19F-NMR (400 MHz in CDCl3): δ ppm: −203.24 (1F).

Workup

  1. washwashed with brine (50 mL)
  2. customdried over anhyd
  3. concentrationNa2SO4 and concentrated under vacuum

Sources & evidence

ORD record
ord-aeeab85edff44591861250f0508d4d43
Source dataset
uspto-grants-2015_03
Patent number
US08987268B2

Reaction notes

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