Triphenylphosphine → HCID 22100824, compound

HRID 1458414Notes

Reaction equation

HRID 1458414 reaction equation
[CH3:1][C:2]1[N:6]([CH2:7][C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]([C:18]#[N:19])=[CH:10][CH:9]=2)[C:5]2[CH:20]=[C:21]([OH:38])[C:22]([O:24][CH:25]3[CH2:30][CH2:29][N:28]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:27][CH2:26]3)=[CH:23][C:4]=2[N:3]=1.[CH2:39]([O:46][C:47]([N:49]1[CH2:54][CH2:53][CH:52](O)[CH2:51][CH2:50]1)=[O:48])[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[CH3:1][C:2]1[N:6]([CH2:7][C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]([C:18]#[N:19])=[CH:10][CH:9]=2)[C:5]2[CH:20]=[C:21]([O:38][CH:52]3[CH2:53][CH2:54][N:49]([C:47]([O:46][CH2:39][C:40]4[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=4)=[O:48])[CH2:50][CH2:51]3)[C:22]([O:24][CH:25]3[CH2:30][CH2:29][N:28]([C:31]([O:33][C:34]([CH3:35])([CH3:37])[CH3:36])=[O:32])[CH2:27][CH2:26]3)=[CH:23][C:4]=2[N:3]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 2794620Benzyl 4-Hydroxy-1-piperidinecarboxylateHCID 5462977Diethyl azodicarboxylateHCID 22100711HCID 22100711, compound

Product 1

HCID 22100824HCID 22100824, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 2-methyl-6-hydroxy-5-(N-(tert-butoxycarbonyl)piperidin-4-yloxy)-1-(4-cyanonaphth-1-yl)methylbenzimidazole (2.8 g) in THF (50 mL) was first added N-benzyloxycarbonyl-4-hydroxypiperidine (1.7 g), PPh3 (1.9 g), and then DEAD (1.2 mL) in a dropwise fashion. After stirring at ambient temperature for 1 hour the solvent was removed and the residue was separated by silica gel chromatography (hexane/ethyl acetate, gradient) to afford 2-methyl-6-(N-(benzyloxycarbonyl)piperidin-4-yloxy)-5-(N-(tert-butoxycarbonyl)piperidin-4-yloxy)-1-(4-cyanonaphth-1-yl)methylbenzimidazole.

Workup

  1. customwas removed
  2. customthe residue was separated by silica gel chromatography (hexane/ethyl acetate, gradient)

Sources & evidence

ORD record
ord-fd99bb4911b44150933198d0722c2c3d
Source dataset
uspto-grants-1998_12
Patent number
US05849759

Reaction notes

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