2-Butyloxirane → 1-(4-Methanesulfonylbenzylamino)hexan-2-ol

HRID 750122Notes

Reaction equation

HRID 750122 reaction equation
[CH3:1][S:2]([C:5]1[CH:12]=[CH:11][C:8]([CH2:9][NH2:10])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[O:13]1[CH:15]([CH2:16][CH2:17][CH2:18][CH3:19])[CH2:14]1>CO>[CH3:1][S:2]([C:5]1[CH:12]=[CH:11][C:8]([CH2:9][NH:10][CH2:14][CH:15]([OH:13])[CH2:16][CH2:17][CH2:18][CH3:19])=[CH:7][CH:6]=1)(=[O:3])=[O:4]

Participants

4

Reactant 2

HCID 150362-ButyloxiraneHCID 574214-Methylsulfonylbenzylamine

Product 1

HCID 230607631-(4-Methanesulfonylbenzylamino)hexan-2-olYield 37.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution (50 ml) of 4-methanesulfonylbenzylamine (5.0 g) and 1,2-epoxyhexane (3.25 g) in methanol was stirred at room temperature for 96 hrs. The reaction-mixture was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (ethyl acetate-ethyl acetate:methanol=10:1) to give the title compound (2.9 g).

Workup

  1. concentrationThe reaction-mixture was concentrated under reduced pressure
  2. customthe obtained residue was purified by silica gel column chromatography (ethyl acetate-ethyl acetate:methanol=10:1)

Sources & evidence

ORD record
ord-a94384d0f50a43b2906522fdf33696ef
Source dataset
uspto-grants-2008_07
Patent number
US07402595B2

Reaction notes

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