1-Benzhydryl-3-[(3-methoxyphenyl)(methylsulfonyl)methylene]azetidine → 1-Benzhydryl-3-[(3-hydroxyphenyl)(methylsulfonyl)methylene]azetidine

HRID 25177Notes

Reaction equation

HRID 25177 reaction equation
[CH:1]([N:14]1[CH2:17][C:16](=[C:18]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([O:29]C)[CH:24]=2)[S:19]([CH3:22])(=[O:21])=[O:20])[CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>ClCCl>[CH:1]([N:14]1[CH2:15][C:16](=[C:18]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([OH:29])[CH:24]=2)[S:19]([CH3:22])(=[O:21])=[O:20])[CH2:17]1)([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 98021961-Benzhydryl-3-[(3-methoxyphenyl)(methylsulfonyl)methylene]azetidine

Product 1

HCID 225653671-Benzhydryl-3-[(3-hydroxyphenyl)(methylsulfonyl)methylene]azetidineYield 28.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

10 cm3 of a 1 M solution of boron tetrabromide in dichloromethane are added, with stirring, to a solution of 1.3 g of 1-benzhydryl-3-[(3-methoxyphenyl)(methylsulfonyl)methylene]azetidine in 100 cm3 of dichloromethane. The stirring is maintained for 16 hours at room temperature. The reaction medium is taken up in 100 cm3 of ice-cold water. The organic phase is washed with 3 times 50 cm3 of water, dried over magnesium sulfate and concentrated to dryness under reduced pressure (2.7 kPa). The residue is precipitated in 150 cm3 of isopropyl ether and then dissolved in 50 cm3 of dichloromethane. The organic phase is washed with 3 times 30 cm3 of a saturated aqueous solution of sodium bicarbonate, decanted off, dried over magnesium sulfate and concentrated to dryness under reduced pressure (2.7 kPa). The residue is precipitated in 80 cm3 of ethyl ether. 0.36 g of 1-benzhydryl-3-[(3-hydroxyphenyl)(methylsulfonyl)methylene]azetidine is obtained from a solid melting at 248° 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), 4.75 (1H, s, NCH), 6.85 (3H, m, 3 CH arom.), 7.25 (3H, m, 3 CH arom.), 7.35 (4H, t, J=7 Hz, 4CH arom.), 7.50 (4H, d, J=7 Hz, 4CH arom.), 9.50 (1H, s, OH)].

Workup

  1. washThe organic phase is washed with 3 times 50 cm3 of water
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  4. customThe residue is precipitated in 150 cm3 of isopropyl ether
  5. dissolutiondissolved in 50 cm3 of dichloromethane
  6. washThe organic phase is washed with 3 times 30 cm3 of a saturated aqueous solution of sodium bicarbonate
  7. customdecanted off
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  10. customThe residue is precipitated in 80 cm3 of ethyl ether

Sources & evidence

ORD record
ord-8a06ed64a7724b3dae100e277a83fc59
Source dataset
uspto-grants-2005_02
Patent number
US06858603B2

Reaction notes

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