Phthalimide → HCID 18467295, compound

HRID 370231Notes

Reaction equation

HRID 370231 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[F:13][C:14]1[CH:33]=[CH:32][C:17]2[C:18]([CH:21]3[CH2:26][CH2:25][N:24]([CH:27]([CH2:30][CH3:31])[CH2:28]O)[CH2:23][CH2:22]3)=[N:19][O:20][C:16]=2[CH:15]=1.[C:34]1(=[O:44])[NH:38][C:37](=[O:39])[C:36]2=[CH:40][CH:41]=[CH:42][CH:43]=[C:35]12.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1.CCOCC>[F:13][C:14]1[CH:33]=[CH:32][C:17]2[C:18]([CH:21]3[CH2:26][CH2:25][N:24]([CH:27]([CH3:28])[CH2:30][CH2:31][N:38]4[C:34](=[O:44])[C:35]5=[CH:43][CH:42]=[CH:41][CH:40]=[C:36]5[C:37]4=[O:39])[CH2:23][CH2:22]3)=[N:19][O:20][C:16]=2[CH:15]=1

Participants

7

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 18467277HCID 18467277, compound

Product 1

HCID 18467295HCID 18467295, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of diethyl azodicarboxylate (DEAD, 4.9 g, 28.3 mmol) in THF (50 ml) was added dropwise to a solution of 2-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperdinyl]-butanol (6.9 g, 23.6 mmol), phthalimide (4.16 gm, 1.2 eq), and triphenylphosphine (7.4 g, 28.3 mmol) in THF (200 ml) at room temperature. The solution was stirred at room temperature for 24 hours. After the reaction, the solvent was stripped and the residue was stirred in ether (200 ml). The insolubles were removed by filtration. The oily residue from concentration of the ether solution was purified by two flash chromatography (SiO2, 75 g; eluted with dichloromethane, DCM, and 1-2% CH3OH in DCM) and SIO2 100 g; eluted with DCM, 11; and 1% CH3OH in DCM, 1.2 l). Two close compounds were separated. The lower compounds on TLC 3.66 g) was treated with HCl/ether in ethanol, and the solid salt was precipitated with hexane. Recrystallization from ethanol and isopropyl ether yielded white crystals 3.26 g, m.p. 210-214° C. dec.

Workup

  1. customAfter the reaction
  2. customThe insolubles were removed by filtration
  3. customThe oily residue from concentration of the ether solution was purified by two flash chromatography (SiO2, 75 g; eluted with dichloromethane, DCM, and 1-2% CH3OH in DCM) and SIO2 100 g
  4. washeluted with DCM, 11
  5. customTwo close compounds
  6. customwere separated
  7. additionThe lower compounds on TLC 3.66 g) was treated with HCl/ether in ethanol
  8. customthe solid salt was precipitated with hexane
  9. customRecrystallization from ethanol and isopropyl ether yielded white crystals 3.26 g, m.p. 210-214° C. dec.

Sources & evidence

ORD record
ord-5a0f7da0c5a9422e89d1e18f323ba37b
Source dataset
uspto-grants-2000_10
Patent number
US06140345

Reaction notes

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