Triphenylphosphine → HCID 9953505, compound

HRID 985722Notes

Reaction equation

HRID 985722 reaction equation
C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[OH:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[N:28]([S:36]([CH3:39])(=[O:38])=[O:37])[C:29]3[C:34]([CH:35]=2)=[CH:33][CH:32]=[CH:31][CH:30]=3)=[CH:23][CH:22]=1.[N:40]1([CH2:46][CH2:47][CH2:48]O)[CH2:45][CH2:44][CH2:43][CH2:42][CH2:41]1>O1CCCC1>[N:40]1([CH2:46][CH2:47][CH2:48][O:20][C:21]2[CH:26]=[CH:25][C:24]([C:27]3[N:28]([S:36]([CH3:39])(=[O:38])=[O:37])[C:29]4[C:34]([CH:35]=3)=[CH:33][CH:32]=[CH:31][CH:30]=4)=[CH:23][CH:22]=2)[CH2:45][CH2:44][CH2:43][CH2:42][CH2:41]1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 66032Piperidine-1-propanolHCID 22507783HCID 22507783, compound

Product 1

HCID 9953505HCID 9953505, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of immobilized triphenylphosphine resin (330 mg, 1.0 meq (Fluka)), and the product of Step E (140 mg, 0.50 mmol) in tetrahydrofuran (6.0 mL) was treated with 3-(piperdin-1-yl)propanol (143 mg, 1.0 mmol) followed by diethylazidodicarboxylate (0.16 mL, 1.1 mmol). The reaction was shaken for 20 hr. and filtered. The filtrate was concentrated in vacuo and the residue purified by silica gel chromatography (methanol/ethyl acetate) to afford pure title compound (97 mg). MS (ESI) m/z 413 (MH+); 1H-NMR (CDCl3) δ 8.13 (d, 1H), 7.59 (d, 1H), 7.50 (d, 2H), 7.36 (m, 2H), 6.97 (d, 2H), 6.68 (s, 1H), 4.08 (t, 2H), 2.72 (s, 3H), 2.4 (m, 6H), 1.63 (m, 6H), 1.45 (m, 2H).

Workup

  1. filtrationand filtered
  2. concentrationThe filtrate was concentrated in vacuo
  3. customthe residue purified by silica gel chromatography (methanol/ethyl acetate)

Sources & evidence

ORD record
ord-a5270f2385eb43ec857a213fafe2697b
Source dataset
uspto-grants-2005_03
Patent number
US06872834B2

Reaction notes

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