Triphenylphosphine → HCID 23151302, compound

HRID 2111829Notes

Reaction equation

HRID 2111829 reaction equation
[CH3:1][C:2]1[N:11]([C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=2)[C:10](=[O:19])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[C:20]([O:24][C:25]([N:27]1[CH2:32][CH2:31][CH:30](O)[CH2:29][CH2:28]1)=[O:26])([CH3:23])([CH3:22])[CH3:21].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>O1CCCC1>[C:20]([O:24][C:25]([N:27]1[CH2:32][CH2:31][CH:30]([O:18][C:15]2[CH:16]=[CH:17][C:12]([N:11]3[C:10](=[O:19])[C:9]4[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=4)[N:3]=[C:2]3[CH3:1])=[CH:13][CH:14]=2)[CH2:29][CH2:28]1)=[O:26])([CH3:23])([CH3:21])[CH3:22]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylateHCID 779440HCID 779440, compoundHCID 5462977Diethyl azodicarboxylate

Product 1

HCID 23151302HCID 23151302, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-methyl-3-(4-hydroxyphenyl)-4 (3H)quinazolinone synthesized according to Example 1-(1) and -(2) (1.0 g, 3.96 mmol), N-(t-butoxycarbonyl)-4-piperidinol (956 mg, 4.75 mmol) and triphenylphosphine (1.56 g, 5.94 mmol) were dissolved in dry tetrahydrofuran (2 mL) in a current of nitrogen, and cooled on an ice bath. Diethylazodicarboxylate (1.17 mL, 5.94 mmol) was dripped in at 0° C., and stirred at room temperature for 48 hours. The solvent was distilled off under reduced pressure, ether was added, the solid precipitate was filtered off, and the filtrate was concentrated. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=7/3), and the target substance (1.1 g, 64%) was obtained as a light brown solid.

Workup

  1. temperaturecooled on an ice bath
  2. customwas dripped in at 0° C.
  3. distillationThe solvent was distilled off under reduced pressure, ether
  4. additionwas added
  5. filtrationthe solid precipitate was filtered off
  6. concentrationthe filtrate was concentrated
  7. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=7/3)
  8. customthe target substance (1.1 g, 64%) was obtained as a light brown solid

Sources & evidence

ORD record
ord-552c18d2387c4d25a7d72defdc87eee5
Source dataset
uspto-grants-2009_04
Patent number
US07521455B2

Reaction notes

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