Triphenylphosphine → 4-[4-(4-Phenyl-3-methyl-phenoxymethyl)-phenyl]-piperidine-1-carboxylic acid tert-butyl ester

HRID 2100681Notes

Reaction equation

HRID 2100681 reaction equation
[C:1]1([C:7]2[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][C:8]=2[CH3:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:15]([O:19][C:20]([N:22]1[CH2:27][CH2:26][CH:25]([C:28]2[CH:33]=[CH:32][C:31]([CH2:34]O)=[CH:30][CH:29]=2)[CH2:24][CH2:23]1)=[O:21])([CH3:18])([CH3:17])[CH3:16].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C1COCC1>[C:15]([O:19][C:20]([N:22]1[CH2:27][CH2:26][CH:25]([C:28]2[CH:33]=[CH:32][C:31]([CH2:34][O:13][C:10]3[CH:11]=[CH:12][C:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)=[C:8]([CH3:14])[CH:9]=3)=[CH:30][CH:29]=2)[CH2:24][CH2:23]1)=[O:21])([CH3:18])([CH3:17])[CH3:16]

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 138684772-Methyl-[1,1'-biphenyl]-4-olHCID 220770564-(4-Hydroxymethylphenyl)piperidine-1-carboxylic acid t-butyl ester

Product 1

HCID 688137374-[4-(4-Phenyl-3-methyl-phenoxymethyl)-phenyl]-piperidine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of 4-phenyl-3-methyl-phenol (1 eq), 4-(4-hydroxymethyl-phenyl)-piperidine-1-carboxylic acid tert-butyl ester (1 eq) and PPh3 (1.5 eq) in dry THF (3 mL) is added 1,1′-(azodicarbonyl)-dipipperidine (1.5 eq) in THF (1 mL). The mixture is stirred at room temperature for 12 hours. After concentration, the residue is purified by silica gel chromatography (10% EtOAc in hexanes) to give 4-[4-(4-phenyl-3-methyl-phenoxymethyl)-phenyl]-piperidine-1-carboxylic acid tert-butyl ester.

Workup

  1. concentrationAfter concentration
  2. customthe residue is purified by silica gel chromatography (10% EtOAc in hexanes)

Sources & evidence

ORD record
ord-fb9dd9bdacd74926aeef28cfcd85e7e4
Source dataset
uspto-grants-2009_08
Patent number
US07572811B2

Reaction notes

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