Triphenylphosphine → HCID 67241724, compound

HRID 1192778Notes

Reaction equation

HRID 1192778 reaction equation
CCOC(/N=N/C(OCC)=O)=O.[OH:13][C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][CH:23]=1)[NH:20][C:19](=[O:24])[CH2:18][CH2:17]2.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:44]([N:51]1[CH2:56][CH2:55][CH:54]([CH2:57]O)[CH2:53][CH2:52]1)([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45]>O1CCCC1.[Cl-].[Na+].O>[O:24]=[C:19]1[CH2:18][CH2:17][C:16]2[C:21](=[CH:22][CH:23]=[C:14]([O:13][CH2:57][CH:54]3[CH2:55][CH2:56][N:51]([C:44]([O:46][C:47]([CH3:48])([CH3:50])[CH3:49])=[O:45])[CH2:52][CH2:53]3)[CH:15]=2)[NH:20]1

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 2764081Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylateHCID 27740406-Hydroxy-3,4-dihydro-2(1H)-quinolinoneHCID 5462977Diethyl azodicarboxylate

Product 1

HCID 67241724HCID 67241724, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
20 °C

Procedure

Diethylazodicarboxylate (40% solution in toluene, 3.3 mL, 7.4 mmol) was added to a mixture of 6-hydroxy-3,4-dihydro-2(1H)-quinolinone (2) (1.0 g, 6.1 mmol), triphenylphosphine (1.607 g, 6.1 mmol), and N-Boc-4-piperidinemethanol (1) (1.32 g, 6.1 mmol) in anhydrous tetrahydrofuran (25 mL) at 0° C. After the addition, the mixture was stirred at 20° C. for 16 h. The reaction mixture was diluted with brine (20 mL) and stirred for 30 min. The mixture was extracted with ethyl acetate (2×30 mL), and washed with brine. The combined organic extract was dried over Na2SO4, and later evaporated on a rotavap. The residue was purified by flash column chromatography on silica gel (230-400 mesh; 8 g) using hexane:ethylacetate solvent mixture. Yield: 3.02 g (some phosphorus side products were present, used without further purification for subsequent step). 1H NMR (400 MHz, CDCl3): δ 7.84 (s, 1H), 6.70 (b.s, 1H), 6.67 (m, 2H), 3.74 (d, 2H), 2.91 (t, 2H), 2.70 (b.t, 2H), 2.59 (m, 2H), 1.93 (b.s, 1H), 1.80 (b.d, 2H), 1.44 (m, 9H), 1.24 (m, 2H).

Workup

  1. additionAfter the addition
  2. stirringstirred for 30 min
  3. extractionThe mixture was extracted with ethyl acetate (2×30 mL)
  4. washwashed with brine
  5. extractionThe combined organic extract
  6. dry with materialwas dried over Na2SO4
  7. customlater evaporated on a rotavap
  8. customThe residue was purified by flash column chromatography on silica gel (230-400 mesh; 8 g)
  9. customused without further purification for subsequent step)

Sources & evidence

ORD record
ord-e33ff9682ba8422aa71c718bac2a0c23
Source dataset
uspto-grants-2014_03
Patent number
US08680279B2

Reaction notes

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