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2-(2-(3-Methoxyphenyl)ethyl)phenol → 1-t-Butoxycarbonyl-4-(2-{2-[2-(3-methoxyphenyl)ethyl]phenoxy}ethyl)piperidine

HRID 743274
Notes
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Reaction equation

HRID 743274 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[OH:17])[CH:6]=[CH:7][CH:8]=1.[C:18]([O:22][C:23]([N:25]1[CH2:30][CH2:29][CH:28]([CH2:31][CH2:32]OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:27][CH2:26]1)=[O:24])([CH3:21])([CH3:20])[CH3:19].CC(C)([O-])C.[K+]>CC(N(C)C)=O>[C:18]([O:22][C:23]([N:25]1[CH2:30][CH2:29][CH:28]([CH2:31][CH2:32][O:17][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[CH2:10][CH2:9][C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=2)[CH2:27][CH2:26]1)=[O:24])([CH3:21])([CH3:20])[CH3:19]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 105854482-(2-(3-Methoxyphenyl)ethyl)phenolHCID 21936070N-Boc-4-[2-(4-Toluenesulfonyloxy)ethyl]piperidineHCID 23665647Potassium tert-butoxide

Product 1

HCID 107655341-t-Butoxycarbonyl-4-(2-{2-[2-(3-methoxyphenyl)ethyl]phenoxy}ethyl)piperidineYield 87.2%

Reagents, catalysts & solvents 1

HCID 31374
Dimethylacetamide
Solvent

Procedure

Following a procedure similar to that described in Example 40(a), 1.20 g of 2-[2-(3-methoxyphenyl) ethyl]phenol (prepared as described in Preparation 20), 2.00 g of 1-t-butoxycarbonyl-4-[2-(p-toluenesulfonyloxy)ethyl]piperidine and 0.590 g of potassium t-butoxide were reacted in 20 ml of dimethylacetamide. The mixture was then worked up as described in Example 40(a), and the crude product thus obtained was purified by column chromatography through silica gel, using a 4:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 2.00 g (yield 86%) of the title compound as a colorless oil.

Workup

  1. customthe crude product thus obtained
  2. customwas purified by column chromatography through silica gel
  3. additionby volume mixture of hexane and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-4642ed30b6274e2f81800e59e9822544
Source dataset
uspto-grants-1996_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05556864

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes