Triphenylphosphine → HCID 86702154, compound

HRID 1776217Notes

Reaction equation

HRID 1776217 reaction equation
C1CCN(C(/N=N/C(N2CCCCC2)=O)=O)CC1.[CH2:19]1[CH2:25][S:22](=[O:24])(=[O:23])[NH:21][CH2:20]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:45][O:46][C:47]1[CH:54]=[C:53]([O:55][CH3:56])[CH:52]=[CH:51][C:48]=1[CH2:49]O>O1CCCC1>[CH3:45][O:46][C:47]1[CH:54]=[C:53]([O:55][CH3:56])[CH:52]=[CH:51][C:48]=1[CH2:49][N:21]1[CH2:20][CH2:19][CH2:25][S:22]1(=[O:24])=[O:23]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 817502,4-Dimethoxybenzyl alcoholHCID 6421571,3-PropanesultamHCID 5702657diazenedicarboxylic acid bis(N,N-piperidide)

Product 1

HCID 86702154HCID 86702154, compoundYield 37.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1,1-(azodicarbonyl) dipiperidine (1.874 g, 7.4 mmol) in anhydrous tetrahydrofuran (10 mL) was added dropwise to a 0° C. solution of 1,3-propanesultam (0.6 g, 4.95 mmol), triphenylphosphine (1.95 g, 7.4 mmol), and 2,4-dimethoxybenzyl alcohol (1.0 g, 6.2 mmol) in anhydrous tetrahydrofuran (20 mL). The resultant solution was stirred at 0° C. for 3 hrs, warmed to room temperature and stirred for a further 16 hrs. The solution was concentrated under reduced pressure and suspended in ethyl acetate/hexanes to precipitate a white solid. The solid was removed by filtration and the filtrate purified by silica gel chromatography (25-70% ethyl acetate/hexanes) to give a pale yellow oil (0.505 g). 1H NMR (CDCl3, 300 MHz) δ 7.31-7.28 (dd, 1H, J=0.6, 7.8 Hz), 6.49-6.44 (m, 2H), 4.17 (s, 2H), 3.81 (s, 3H), 3.80 (s, 3H), 3.19-3.13 (m, 4H), 2.32-2.23 (m, 2H).

Workup

  1. concentrationThe solution was concentrated under reduced pressure
  2. customto precipitate a white solid
  3. customThe solid was removed by filtration
  4. customthe filtrate purified by silica gel chromatography (25-70% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-e7e696ba433045b4a9cef8af7018338b
Source dataset
uspto-grants-2016_02
Patent number
US09265772B2

Reaction notes

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