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

HRID 2100656Notes

Reaction equation

HRID 2100656 reaction equation
[CH:1]1([C:7]2[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][C:8]=2[CH3:14])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]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>C(Cl)Cl>[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]([CH:1]4[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]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 3085662Phenol, cyclohexyl-3(or 4)-methyl-HCID 220770564-(4-Hydroxymethylphenyl)piperidine-1-carboxylic acid t-butyl ester

Product 1

HCID 688156794-[4-(4-Cyclohexyl-3-methyl-phenoxymethyl)-phenyl]-piperidine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 4-cyclohexyl-3-methyl-phenol (65 mg, 0.34 mmol, 1 eq.), 4-(4-Hydroxymethyl-phenyl)-piperidine-1-carboxylic acid tert-butyl ester (100 mg, 0.34 mmol, 1 eq.) and PPh3 (134 mg, 0.51 mmol, 1.5 eq.) in dry DCM (3 mL) is added 1,1′-(azodicarbonyl)-dipipperidine (129 mg, 0.51 mmol, 1.5 eq.) in DCM (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-cyclohexyl-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-3a04e820385c4cc7880cc28496f5756d
Source dataset
uspto-grants-2009_08
Patent number
US07572811B2

Reaction notes

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