HCID 25139482, compound → HCID 25140182, compound

HRID 1669123Notes

Reaction equation

HRID 1669123 reaction equation
[CH2:1]([C:3]1[N:4]=[N+:5]([O-:25])[C:6]2[CH:15]=[C:14]3[C:10]([CH2:11][CH:12]([CH2:16][CH2:17][O:18]C4CCCCO4)[CH2:13]3)=[CH:9][C:7]=2[N:8]=1)[CH3:2]>CS(O)(=O)=O.CO>[CH2:1]([C:3]1[N:4]=[N+:5]([O-:25])[C:6]2[CH:15]=[C:14]3[C:10]([CH2:11][CH:12]([CH2:16][CH2:17][OH:18])[CH2:13]3)=[CH:9][C:7]=2[N:8]=1)[CH3:2]

Participants

4

Reactant 1

HCID 25139482HCID 25139482, compound

Product 1

HCID 25140182HCID 25140182, compoundYield 94.4%

Reagents, catalysts & solvents 2

HCID 6395Methanesulfonic AcidCatalystHCID 887MethanolSolvent

Conditions

Temperature
20 °C

Procedure

Methanesulfonic acid (3 drops) was added to a stirred solution of tetrahydropyranyl ether 160 (1.10 g, 3.2 mmol) in MeOH (30 mL) and the mixture was stirred at 20° C. for 1 h. The solvent was evaporated and the residue purified by chromatography, eluting with 5% MeOH/DCM, to give 1-oxide 161 (783 mg, 94%) as a yellow solid: mp 96-99° C.; 1H NMR δ 8.23 (s, 1H, H-9), 7.72 (s, 1H, H-5), 3.80 (t, J=6.5 Hz, 2H, CH2O), 3.25-3.33 (m, 2H, H-6, H-8), 3.02 (q, J=7.6 Hz, 2H, CH2), 2.68-2.86 (m, 3H, H-6, H-7, H-8), 1.84 (q, J=6.5 Hz, 2H, CH2), 1.43 (t, J=7.6 Hz, 3H, CH3), 1.40-1.45 (m, 1H, OH); 13C NMR δ 167.1, 153.8, 147.9, 147.6, 132.3, 122.7, 114.3, 61.5, 39.4, 39.1, 37.9, 37.5, 30.6, 12.3; HRMS (FAB+) calcd for C14H18N3O2 (MH+) m/z 260.1399, found 260.1397.

Workup

  1. customThe solvent was evaporated
  2. customthe residue purified by chromatography
  3. washeluting with 5% MeOH/DCM

Sources & evidence

ORD record
ord-5058c2a5e55a415d861ac8e813fed56b
Source dataset
uspto-grants-2011_08
Patent number
US07989451B2

Reaction notes

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