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Phthalimide → HCID 86701547, compound

HRID 2173979
Notes
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Reaction equation

HRID 2173979 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH2:29]O)[C:5]([CH2:21][O:22]C2CCCCO2)=[C:6]2[C:10]=1[N:9]([S:11]([C:14]1[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=1)(=[O:13])=[O:12])[CH:8]=[CH:7]2.[C:31]1(=[O:41])[NH:35][C:34](=[O:36])[C:33]2=[CH:37][CH:38]=[CH:39][CH:40]=[C:32]12.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[OH:22][CH2:21][C:5]1[C:4]([CH2:29][N:35]2[C:31](=[O:41])[C:32]3[C:33](=[CH:37][CH:38]=[CH:39][CH:40]=3)[C:34]2=[O:36])=[CH:3][C:2]([CH3:1])=[C:10]2[C:6]=1[CH:7]=[CH:8][N:9]2[S:11]([C:14]1[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=1)(=[O:13])=[O:12]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 86701545HCID 86701545, compound

Product 1

HCID 86701547HCID 86701547, compound

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Procedure

To a solution of (±)-(7-methyl-4-(((tetrahydro-2H-pyran-2-yl)oxy)methyl)-1-tosyl-1H-indol-5-yl)methanol (Example 52-C) (210 mg, 0.49 mmol), phthalimide (144 mg, 0.98 mmol), and PPh3 (385 mg, 1.47 mmol) in THF (5 mL) was added DIAD (0.29 mL, 1.48 mmol) at 0° C., and then the mixture was stirred at room temperature for 3.5 h. The reaction was then concentrated and partially purified by SiO2 column chromatography (heptane/EtOAc=1/0 to 6/4). A solution of the resulting residue and 4M HCl in dioxane (4 mL) in MeOH (10 mL) was stirred at room temperature for 0.5 h. The reaction mixture was poured into 5% aq. NaHCO3. The basic mixture was extracted with CH2Cl2. The organics extract was washed with H2O and brine, dried over Na2SO4, and then filtered. Concentration of the filtrate gave a residue which was purified by SiO2 column chromatography (heptane/EtOAc=6/4 to 3/7) to give the title compound. 1H NMR (400 MHz, DMSO-d6) δ 7.76-7.95 (m, 5H), 7.59 (d, J=8.34 Hz, 2H), 7.38 (d, J=8.34 Hz, 2H), 7.06 (d, J=4.04 Hz, 1H), 6.90 (s, 1H), 5.08 (t, J=5.31 Hz, 1H), 4.91 (s, 2H), 4.85 (d, J=5.31 Hz, 2H), 2.38 (s, 3H), 2.33 (s, 3H).

Workup

  1. concentrationThe reaction was then concentrated
  2. custompartially purified by SiO2 column chromatography (heptane/EtOAc=1/0 to 6/4)
  3. stirringA solution of the resulting residue and 4M HCl in dioxane (4 mL) in MeOH (10 mL) was stirred at room temperature for 0.5 h
  4. additionThe reaction mixture was poured into 5% aq. NaHCO3
  5. extractionThe basic mixture was extracted with CH2Cl2
  6. extractionThe organics extract
  7. washwas washed with H2O and brine
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. customConcentration of the filtrate gave a residue which
  11. customwas purified by SiO2 column chromatography (heptane/EtOAc=6/4 to 3/7)

Sources & evidence

ORD record
ord-70254cc737a84dcfbe0676d865b11072
Source dataset
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09056874B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes