Tert-butyl 2-{2-[(4-methylbenzenesulfonyl)oxy]ethyl}piperidine-1-carboxylate → 1-t-Butoxycarbonyl-2-(2-{2-[2-(4-ethylphenyl)ethyl]phenoxy}ethyl)piperidine

HRID 743307Notes

Reaction equation

HRID 743307 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[OH:17])=[CH:5][CH:4]=1)[CH3:2].CC(C)([O-])C.[K+].[C:24]([O:28][C:29]([N:31]1[CH2:36][CH2:35][CH2:34][CH2:33][CH:32]1[CH2:37][CH2:38]OS(C1C=CC(C)=CC=1)(=O)=O)=[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][CH2:33][CH:32]1[CH2:37][CH2:38][O:17][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[CH2:10][CH2:9][C:6]1[CH:7]=[CH:8][C:3]([CH2:1][CH3:2])=[CH:4][CH:5]=1)=[O:30])([CH3:27])([CH3:26])[CH3:25]

Participants

5

Reactant 3

HCID 15734710Tert-butyl 2-{2-[(4-methylbenzenesulfonyl)oxy]ethyl}piperidine-1-carboxylateHCID 194239982-[2-(4-Ethylphenyl)ethyl]phenolHCID 23665647Potassium tert-butoxide

Product 1

HCID 194238691-t-Butoxycarbonyl-2-(2-{2-[2-(4-ethylphenyl)ethyl]phenoxy}ethyl)piperidineYield 99.3%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

Following a procedure similar to that described in Example 40(a), 1.00 g of 2-[2-(4-ethylphenyl)ethyl]phenol (prepared as described in Preparation 26), 0.496 g of potassium t-butoxide and 1.70 g of 1-t-butoxycarbonyl-2-[2-(p-toluenesulfonyloxy)ethyl]piperidine 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 1.92 g (yield 99%) 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-657e56a07a3542e39d6c8423733e01af
Source dataset
uspto-grants-1996_09
Patent number
US05556864

Reaction notes

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