Reacción #53457

Ecuación de reacción

1-benzhydryl-3-[(2-methoxyphenyl)(methylsulfonyl)methylene]azetidine

boron tribromide

→

1-benzhydryl-3-[(2-hydroxyphenyl)(methylsulfonyl)methylene]azetidine

Rendimiento 51.7%

Disolventes

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrothe residue obtained
2. 2
   Otrois purified by chromatography on a silica gel column (particle size 0.04-0.06 mm, diameter 4 cm, height 30 cm) at a nitrogen pressure of 0.5 bar with dichloromethane as eluent
3. 3
   Otrocollecting 40 cm3 fractions
4. 4
   Concentraciónconcentrated to dryness under reduced pressure (2.7 kPa)
5. 5
   OtroThe solid obtained
6. 6
   Otrois crystallized from 40 cm3 of ethyl ether

Procedimiento

On carrying out the operation according to the procedure of Example 32 starting with 1.4 g of 1-benzhydryl-3-[(2-methoxyphenyl)(methylsulfonyl)methylene]azetidine, 10 cm3 of a 1 M solution of boron tribromide and 100 cm3 of dichloromethane, the residue obtained is purified by chromatography on a silica gel column (particle size 0.04-0.06 mm, diameter 4 cm, height 30 cm) at a nitrogen pressure of 0.5 bar with dichloromethane as eluent and collecting 40 cm3 fractions. Fractions 15 to 34 are combined and concentrated to dryness under reduced pressure (2.7 kPa). The solid obtained is crystallized from 40 cm3 of ethyl ether. 0.7 g of 1-benzhydryl-3-[(2-hydroxyphenyl)(methylsulfonyl)methylene]azetidine is obtained melting at 196° C. [NMR spectrum in DMSO-d6, T=300K, δ in ppm (300 MHz): 3.00 (3H, s, SCH3), 3.60 (2H, s, NCH2), 4.20 (2H, s, NCH2), 4.75 (1H, s, NCH), 6.85 (1H, t, J=7 Hz, CH arom.), 6.90 (1H, d, J=7 Hz, CH arom.), 7.20 (4H, m, 4CH arom.), 7.30 (4H, t, J=7 Hz, 4CH arom.), 7.48 (4H, d, J=7 Hz, 4CH arom.), 9.90 (1H, s, OH)].

Fuente