2-(2-Phenylethyl)phenol → 1-t-Butoxycarbonyl-2-(2-[2-(2-phenylethyl)phenoxy]ethyl}piperidine

HRID 743289Notes

Reaction equation

HRID 743289 reaction equation
[C:1]1([CH2:7][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[OH:15])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC(C)([O-])C.[K+].[C:22]([O:26][C:27]([N:29]1[CH2:34][CH2:33][CH2:32][CH2:31][CH:30]1[CH2:35][CH2:36]OS(C1C=CC(C)=CC=1)(=O)=O)=[O:28])([CH3:25])([CH3:24])[CH3:23]>CC(N(C)C)=O>[C:22]([O:26][C:27]([N:29]1[CH2:34][CH2:33][CH2:32][CH2:31][CH:30]1[CH2:35][CH2:36][O:15][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[CH2:8][CH2:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)=[O:28])([CH3:25])([CH3:24])[CH3:23]

Participants

5

Reactant 3

HCID 27490412-(2-Phenylethyl)phenolHCID 15734710Tert-butyl 2-{2-[(4-methylbenzenesulfonyl)oxy]ethyl}piperidine-1-carboxylateHCID 23665647Potassium tert-butoxide

Product 1

HCID 106928911-t-Butoxycarbonyl-2-(2-[2-(2-phenylethyl)phenoxy]ethyl}piperidineYield 75.6%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

Following a procedure similar to that described in Example 40(a), 0.930 g of 2-(2-phenylethyl)phenol (prepared as described in Preparation 19), 0.527 g of potassium t-butoxide and 1.66 g of 1-t-butoxycarbonyl-2-[2-(p-toluenesulfonyloxy)ethyl]piperidine were reacted in 20 ml of dimethylacetamide. The mixture was then worked lap 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 1.34 g (yield 75%) 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-1decb7bc171b4a769638960929e47442
Source dataset
uspto-grants-1996_09
Patent number
US05556864

Reaction notes

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