1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 86758837, compound

HRID 1058858Notes

Reaction equation

HRID 1058858 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[CH2:6]O.[CH3:14][O:15][C:16](=[O:34])[CH:17](P(OCC)(OCC)=O)[NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20].C1CCN2C(=NCCC2)CC1>C(Cl)Cl.[Mn]>[C:22]([O:21][C:19]([NH:18]/[C:17](=[CH:6]\[C:5]1[CH:8]=[CH:9][C:10]([N+:11]([O-:13])=[O:12])=[C:3]([O:2][CH3:1])[CH:4]=1)/[C:16]([O:15][CH3:14])=[O:34])=[O:20])([CH3:25])([CH3:24])[CH3:23]

Participants

6

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 6029613-Methoxy-4-nitrobenzyl alcoholHCID 21572878HCID 21572878, compound

Product 1

HCID 86758837HCID 86758837, compound

Reagents, catalysts & solvents 2

HCID 23930ManganeseCatalystHCID 6344DichloromethaneSolvent

Procedure

Activated manganese IV oxide (26 g) was added to a mixture of 3-methoxy-4-nitrobenzylalcohol (5.26 g, 28.7 mmol), N-(t-Butyloxycarbonyl)-α-(diethylphosphono)glycine methylester (described in WO99/47547) (8.91 g, 27.4 mmol) and DBU (4.29 ml, 28.7 mmol) in DCM (150 ml) at 0°. The mixture was stirred at RT overnight then filtered. The filtrate was washed with dil. HCl, dried (Na2SO4) and evaporated in vacuo. Recrystallisation from MeOH gave the title compound as pale brown crystals (4.6 g). δH (DMSO d6) 8.94 (1H, br s), 7.91 (1H, d, J 8.4 Hz), 7.56 (1H, d, J 1.5 Hz), 7.36 (1H, dd, J 8.5, 1.3 Hz), 7.12 (1H, br s), 3.92 (3H, s), 3.75 (3H, s), 1.37 (9H, s). m/z (ES+, 70V) 375 (M++Na).

Workup

  1. customat 0°
  2. filtrationthen filtered
  3. washThe filtrate was washed with dil. HCl
  4. dry with materialdried (Na2SO4)
  5. customevaporated in vacuo
  6. customRecrystallisation from MeOH

Sources & evidence

ORD record
ord-a3735276488847139e3a634cc932e013
Source dataset
uspto-grants-2003_02
Patent number
US06518283B1

Reaction notes

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