4-Methoxybenzyl alcohol → HCID 18449403, compound

HRID 656391Notes

Reaction equation

HRID 656391 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[CH2:9][C:8]1([C:16](=[O:17])[NH:15][C:14](=[O:18])[NH:13]1)[CH2:7]2)([O-:3])=[O:2].[CH3:19][O:20][C:21]1[CH:28]=[CH:27][C:24]([CH2:25]O)=[CH:23][CH:22]=1.N(C(OCC)=O)=NC(OCC)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[CH3:19][O:20][C:21]1[CH:28]=[CH:27][C:24]([CH2:25][N:15]2[C:16](=[O:17])[C:8]3([CH2:7][C:6]4[C:10](=[CH:11][CH:12]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=4)[CH2:9]3)[NH:13][C:14]2=[O:18])=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 77384-Methoxybenzyl alcoholHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 16638331HCID 16638331, compound2×

Product 1

HCID 18449403HCID 18449403, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (±)-5′-nitro-spiro[imidazolidine-4,2′-indane]-2,5-dione (1.4 g, 5.66 mmol, described in Intermediate 6), 4-methoxybenzyl alcohol (0.94 g, 6.80 mmol), diethyl azodicarboxylate (1.48 g, 8.49 mmol), and triphenylphosphine (2.23 g, 8.49 mmol) in THF (15 mL) was stirred at ambient temperature for 3 days. The solvent was removed under reduced pressure and the residue was partitioned between saturated aqueous NaHCO3 (15 mL) and CH2Cl2 (50 mL). The organic layer was dried (Na2SO4), filtered, and concentrated under reduced pressure. The crude product was purified by silica gel chromatography, eluting with a gradient of hexane:EtOAc—90:10 to 60:40, to give the title compound. MS: m/z=368 (M+1).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was partitioned between saturated aqueous NaHCO3 (15 mL) and CH2Cl2 (50 mL)
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified by silica gel chromatography
  7. washeluting with a gradient of hexane

Sources & evidence

ORD record
ord-5f80f8d9ecfb406c8da3315d9c438e56
Source dataset
uspto-grants-2011_12
Patent number
US08071771B2

Reaction notes

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