Triphenylphosphine → HCID 67239290, compound

HRID 1192779Notes

Reaction equation

HRID 1192779 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[CH2:54][CH:53]([CH2:55]O)[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][CH2:55][CH:53]3[CH2:54][N:51]([C:44]([O:46][C:47]([CH3:48])([CH3:50])[CH3:49])=[O:45])[CH2:52]3)[CH:15]=2)[NH:20]1

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 27740406-Hydroxy-3,4-dihydro-2(1H)-quinolinoneHCID 5462977Diethyl azodicarboxylateHCID 10583745tert-Butyl 3-(hydroxymethyl)azetidine-1-carboxylate

Product 1

HCID 67239290HCID 67239290, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
20 °C

Procedure

Diethylazodicarboxylate (40% solution in toluene, 3.4 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 1-boc-azetidine-3-yl-methanol 18 (1.148 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 (2×50 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; 24 g) using dichloromethane:methanol:methanol (95:5:0.05) solvent mixture. Yield: 4.02 g (some phosphorus side products were present, used without further purification for subsequent step). 1H NMR (400 MHz, CDCl3): δ 6.70 (m, 2H), 6.63 (m, 1H), 4.02 (m, 4H), 3.96 (m, 1H), 3.75 (m, 2H), 2.91 (t, 2H), 2.58 (t, 2H), 1.41 (m, 9H).

Workup

  1. additionAfter the addition
  2. stirringstirred for 30 min
  3. extractionThe mixture was extracted with ethyl acetate (2×50 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; 24 g)
  9. customused without further purification for subsequent step)

Sources & evidence

ORD record
ord-156d549a4ffd45f59d12e5efcdaa5f67
Source dataset
uspto-grants-2014_03
Patent number
US08680279B2

Reaction notes

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