Tetrahydrofuran → HCID 57510065, compound

HRID 624179Notes

Reaction equation

HRID 624179 reaction equation
[CH2:1]([NH:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14]([N:16]2[CH2:24][C:23]3[C:18](=[CH:19]C=C(C=C)[CH:22]=3)[CH2:17]2)=[O:15])=[CH:9][CH:8]=1)=[O:6])[CH2:2][CH3:3].C[N+]1([O-])CC[O:31]CC1.[O:35]1[CH2:39][CH2:38][CH2:37][CH2:36]1>CC(O)C.[Os](=O)(=O)(=O)=O>[OH:31][CH:38]([C:37]1[CH:19]=[C:18]2[C:23](=[CH:22][CH:36]=1)[CH2:24][N:16]([C:14]([NH:13][C:10]1[CH:11]=[CH:12][C:7]([C:5]([NH:4][CH2:1][CH2:2][CH3:3])=[O:6])=[CH:8][CH:9]=1)=[O:15])[CH2:17]2)[CH2:39][OH:35]

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 82029Methyl morpholine oxideHCID 57510040HCID 57510040, compound

Product 1

HCID 57510065HCID 57510065, compound

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 3776IsopropanolSolvent

Procedure

A suspension of N-[4-(propylcarbamoyl)phenyl]-5-vinyl-1,3-dihydro-2H-isoindole-2-carboxamid (0.03 g, 0.086 mmol) in tetrahydrofuran (1 ml) and 2-propanol (0.3 ml) was treated with osmium tetroxide (2.5% wt. % solution in 2-methyl-2-propanol) (0.108 ml, 8.59 μmol). The reaction mixture was treated with N-methylmorpholine-N-oxide (0.030 g, 0.258 mmol). The reaction mixture was allowed to stir at room temperature overnight, quenched with aqueous sodium sulfite solution and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, and concentrated under vacuum. Flash chromatography provided the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 8.55 (s, 1H), 8.25 (t, J=5.7 Hz, 1H), 7.74-7.78 (m, 2H), 7.63-7.68 (m, 2H), 7.27-7.33 (m, 3H), 5.24 (d, J=4.2 Hz, 1H), 4.75-4.77 (bs, 4H), 4.70 (t, J=5.8 Hz, 1H), 4.53-4.59 (m, 1H), 3.43 (t, J=5.8 Hz, 2H), 3.16-3.23 (m, 2H), 1.42-1.63 (m, 2H), 0.89 (t, J=7.4 Hz, 3H); MS (ESI(+)) m/e 384 (M+H)+.

Workup

  1. customquenched with aqueous sodium sulfite solution
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-24bcfa9f94304208b414373866b6261e
Source dataset
uspto-grants-2016_04
Patent number
US09302989B2

Reaction notes

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