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

HRID 743266Notes

Reaction equation

HRID 743266 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.CC(C)([O-])C.[K+].[C:24]([O:28][C:29]([N:31]1[CH2:36][CH2:35][CH2:34][CH:33]([CH2:37]OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:32]1)=[O:30])([CH3:27])([CH3:26])[CH3:25]>CC(N(C)C)=O>[C:24]([O:28][C:29]([N:31]1[CH2:36][CH2:35][CH2:34][CH:33]([CH2:37][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)[CH2:32]1)=[O:30])([CH3:27])([CH3:25])[CH3:26]

Participants

5

Reactant 3

HCID 105854482-(2-(3-Methoxyphenyl)ethyl)phenolHCID 18369320Tert-butyl 3-((P-tolylsulfonyloxy)methyl)piperidine-1-carboxylateHCID 23665647Potassium tert-butoxide

Product 1

HCID 117966521-t-Butoxycarbonyl-3-{2-[2-(3-methoxyphenyl)ethyl]phenoxymethyl}piperidineYield 74%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

Following a procedure similar to that described in Example 40, 0.790 g of 2-[2-(3-methoxyphenyl)ethyl]phenol (prepared as described in Preparation 20), 0.388 g of potassium t-butoxide and 1.28 g of 1-t-butoxycarbonyl-3-(p-toluenesulfonyloxymethyl)piperidine were reacted in 15 ml of dimethylacetamide. The mixture was then worked up as described in Example 40, 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 1.09 g (yield 74%) 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-7f2d6c45182547a78fceada03d145ce2
Source dataset
uspto-grants-1996_09
Patent number
US05556864

Reaction notes

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