Reaction #1869178

Reaction equation

compound

1-butyl-3-isobutyl-1,3,8-triazaspiro[4.5]decane-2,4-dione

N,N-diisopropylethylamine

benzenesulfonylchloride resin

TsCl

6-phenylhexanol

→

title compound

Yield 58.9%

1-butyl-3-isobutyl-8-(6-phenylhexyl)-1,3,8-triazaspiro[4.5]decane-2,4-dione hydrochloride

Yield 58.9%

Solvents

acetonitrile

Conditions

Workup

1. 1
   Filtrationfiltrated
2. 2
   WashThe resin was washed with acetonitrile (3 mL, three times)
3. 3
   WashThe filtrate and rinsed solution
4. 4
   Concentrationconcentrated
5. 5
   OtherThe residue was purified by column chromatography on silica gel (chloroform:methanol=25:1)
6. 6
   workup.ADDITIONadded 4N hydrochloric acid in ethyl acetate
7. 7
   Concentrationconcentrated

Procedure

To a solution of the compound prepared in Example 1 (28 mg) and N,N-diisopropylethylamine (155 mg) in acetonitrile (3 mL) were added benzenesulfonylchloride resin (Argonaut, product name PS-TsCl, product number 800276, 1.22 mmol/g, 0.20 mmol) (164 mg) and sulfonyl resin (175 mg) which is prepared from 6-phenylhexanol (345 mg). The mixture was stirred for 18 hours at 70° C. and then filtrated. The resin was washed with acetonitrile (3 mL, three times). The filtrate and rinsed solution were combined and concentrated. The residue was purified by column chromatography on silica gel (chloroform:methanol=25:1), added 4N hydrochloric acid in ethyl acetate and concentrated to give the title compound (28 mg) having the following physical data.

Source