Réaction #53461

Équation de réaction

water

tetrabutylammonium fluoride

1-benzhydryl-3-{[3-(tert-butyldimethylsiloxymethyl)phenyl](methylsulfonyl)methylene}azetidine

→

1-benzhydryl-3-[(3-hydroxymethylphenyl)(methylsulfonyl)methylene]azetidine

Rendement 57.8%

Solvants

tetrahydrofuran

ethyl acetate

tetrahydrofuran

Conditions de réaction

Traitement

1. 1
   Autreclose to 20° C.
2. 2
   AutreThe organic phase is decanted off
3. 3
   Extractionextracted
4. 4
   Séchagedried over anhydrous magnesium sulfate
5. 5
   Concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
6. 6
   AutreThe residue obtained
7. 7
   Autreis purified by chromatography on a silica gel column (particle size 0.04-0.06 mm, diameter 2 cm, height 30 cm), at a nitrogen pressure of 0.5 bar with a mixture of dichloromethane and ethanol (95/5 by volume) as eluent
8. 8
   Autrecollecting 60 cm3 fractions
9. 9
   Concentrationconcentrated to dryness under reduced pressure (2.7 kPa)

Mode opératoire

4 cm3 of a 1 M solution of tetrabutylammonium fluoride in tetrahydrofuran are added to a solution, cooled to 5° C., of 1.1 g 1-benzhydryl-3-{[3-(tert-butyldimethylsiloxymethyl)phenyl](methylsulfonyl)methylene}azetidine in 10 cm3 of tetrahydrofuran. The mixture is stirred for 3 hours at a temperature close to 20° C. and then taken up in 100 cm3 of ethyl acetate and twice 50 cm3 of water. The organic phase is decanted off, extracted, dried over anhydrous magnesium sulfate and concentrated to dryness under reduced pressure (2.7 kPa). The residue obtained is purified by chromatography on a silica gel column (particle size 0.04-0.06 mm, diameter 2 cm, height 30 cm), at a nitrogen pressure of 0.5 bar with a mixture of dichloromethane and ethanol (95/5 by volume) as eluent and collecting 60 cm3 fractions. Fractions 4 to 6 are combined and concentrated to dryness under reduced pressure (2.7 kPa). 0.5 g of 1-benzhydryl-3-[(3-hydroxymethylphenyl)(methylsulfonyl)methylene]azetidine is obtained in the form of a white solid melting at 152° C. [NMR spectrum in DMSO-d6, T=300K, δ in ppm (300 MHz): 2.95 (3H, s, SCH3), 3.80 (2H, s, NCH2), 4.20 (2H, s, NCH2), 4.50 (2H, d, J=5 Hz, OCH2), 4.75 (1H, s, NCH), 5.25 (1H, t, J=5 Hz, OH), 7.20 (2H, t, J=7 Hz, 2CH arom.), 7.30 (8H, m. 8CH arom.), 7.45 (4H, d, J=7 Hz, 4 CH arom.)].

Source