Phenol → 4-[(4-Bromophenyl)-phenoxymethyl]-piperidine-1-carboxylic acid tert-butyl ester

HRID 1726123Notes

Reaction equation

HRID 1726123 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH:14]([C:16]2[CH:21]=[CH:20][C:19]([Br:22])=[CH:18][CH:17]=2)[OH:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:23]1(O)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([CH:14]([C:16]2[CH:21]=[CH:20][C:19]([Br:22])=[CH:18][CH:17]=2)[O:15][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 996PhenolHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 57603260Tert-butyl 4-((4-bromophenyl)(hydroxy)methyl)piperidine-1-carboxylate

Product 1

HCID 689707094-[(4-Bromophenyl)-phenoxymethyl]-piperidine-1-carboxylic acid tert-butyl esterYield 48%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-[(4-bromophenyl)-hydroxymethyl]-piperidine-1-carboxylic acid tert-butyl ester (370 mg, 1.00 mmol), phenol (141 mg, 1.50 mmol) and Ph3P (393 mg, 1.50 mmol) in THF (6 mL) at room temperature was added DIAD (0.295 mL, 1.50 mmol) dropwise. The mixture was stirred at room temperature for 2.5 hours. Aqueous work-up and purification gave 4-[(4-bromophenyl)-phenoxymethyl]-piperidine-1-carboxylic acid tert-butyl ester as a colorless oil (213 mg, 48%).

Workup

  1. customAqueous work-up and purification

Sources & evidence

ORD record
ord-ddc8165991964ecba1b7fbd281706e61
Source dataset
uspto-grants-2009_02
Patent number
US07491735B2

Reaction notes

Loading…