1,3-Cyclohexadiene → HCID 11750599, compound

HRID 2054760Notes

Reaction equation

HRID 2054760 reaction equation
[P:1]([O:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([C@@H:26]2[CH:30]=[C:29]([C:31]3[CH:36]=[C:35]([F:37])[CH:34]=[CH:33][C:32]=3[F:38])[CH2:28][N:27]2[C:39]([N:41]([CH3:43])[CH3:42])=[O:40])[CH:21]=1)([O:11]CC1C=CC=CC=1)([O:3]CC1C=CC=CC=1)=[O:2].C1CCC=CC=1>CO.[Pd]>[P:1]([OH:11])([OH:3])([O:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([C@@H:26]2[CH:30]=[C:29]([C:31]3[CH:36]=[C:35]([F:37])[CH:34]=[CH:33][C:32]=3[F:38])[CH2:28][N:27]2[C:39]([N:41]([CH3:42])[CH3:43])=[O:40])[CH:21]=1)=[O:2]

Participants

5

Reactant 2

HCID 116051,3-CyclohexadieneHCID 59656620HCID 59656620, compound

Product 1

HCID 11750599HCID 11750599, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Dibenzyl 3-{(2S)-4-(2,5-difluorophenyl)-1-[(dimethylamino)carbonyl]-2,5-dihydro-1H-pyrrol-2-yl)phenyl phosphate (8-1, 108 mg, 0.18 mmol) was dissolved in 4:1 MeOH:cyclohexadiene (2 mL) and treated with 10% Palladium on carbon (100 mg). The reaction was stirred vigorously for 15 min, and then filtered over celite using MeOH to wash the compound throughly from the celite. The washings were concentrated and purified by reverse phase column chromatography (C-8, 10-90% CH3CN/H2O with 0.1% TFA gradient) to provide 3-{(2S)-4-(2,5-difluorophenyl)-1-[(dimethylamino)carbonyl]-2,5-dihydro-1H-pyrrol-2-yl}phenyl dihydrogen phosphate (8-2) as a white solid: 1H NMR (300 MHz, CD3OD) δ 7.20 (m. 7H), 6.42 (br s, 1H), 6.08 (m, 1H), 5.00 (dd, J=14.0, 3.6 Hz, 1H), 4.55 (d, J=14.0 Hz, 1H), 2.92 (s, 6H). LRMS m/z (M+H) 425.4 found, 425.3 required.

Workup

  1. filtrationfiltered over celite
  2. washto wash the compound throughly from the celite
  3. concentrationThe washings were concentrated
  4. custompurified by reverse phase column chromatography (C-8, 10-90% CH3CN/H2O with 0.1% TFA gradient)

Sources & evidence

ORD record
ord-43d6edcb1cda49b59200c0727c36f4c4
Source dataset
uspto-grants-2008_02
Patent number
US07329762B2

Reaction notes

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