Triphenylphosphine → HCID 12017322, compound

HRID 1860638Notes

Reaction equation

HRID 1860638 reaction equation
[CH2:1]([C:8]([CH3:34])([CH2:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH2:24][CH2:25][NH:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][N+:28]=2[O-])=[CH:18][CH:17]=1)[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C(O)(=O)C.[Fe]>[CH2:1]([C:8]([CH3:34])([CH2:15][C:16]1[CH:17]=[CH:18][C:19]([O:22][CH2:23][CH2:24][CH2:25][NH:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=2)=[CH:20][CH:21]=1)[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 11776TriphenylphosphineHCID 178471294HCID 178471294, compound

Product 1

HCID 12017322HCID 12017322, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

To ethyl 3-benzyl-3-methyl-4-(4-{3-[(1-oxidopyridin-2-yl)amino]propoxy}phenyl)butanoate (322 mg) and PPh3 (220 mg, 0.84 mmol) in glacial acetic acid (5 mL) was added Fe powder (58 mg, 1.0 mmol). The reaction mixture was refluxed for 20 min and cooled to RT. The iron was removed by using a magnet and the mixture concentrated to an oil. The oil was purified by flash column chromatography using 80% EtOAc/hexane as eluent. Obtained was an oily ethyl 3-benzyl-3-methyl-4-{4-[3-(pyridin-2-ylamino) propoxy]phenyl}butan-oate (218 mg, 0.48 mmol, 2 step yield 55%). LC-MS (MH+)=447. H NMR (DMSO-d6) δ0.81 (s, 3H), 1.20 (t, 3H), 1.95 (m, 2H), 2.02 (s, 2H), 2.54-2.78 (m, 4H), 3.37 (q, 2H), 4.02 (t, 2H), 4.09 (q, 2H), 6.43 (m, 2H), 6.55 (t, 1H), 6.85 (d, 2h), 7.06 (d, 2H), 7.15 (d, 2H), 7.21 (dd, 1H), 7.28 (d, 2H), 7.33 (dd, 1H), 7.95 (d, 1H).

Workup

  1. temperatureThe reaction mixture was refluxed for 20 min
  2. customThe iron was removed
  3. concentrationthe mixture concentrated to an oil
  4. customThe oil was purified by flash column chromatography
  5. customObtained

Sources & evidence

ORD record
ord-c4634a92eefc429d8eab1506be35824d
Source dataset
uspto-grants-2003_03
Patent number
US06531494B1

Reaction notes

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