Methanesulfonyl chloride → 3-(4-tert-Butylphenyl)-3-chloro-1-(diphenylmethyl)azetidine

HRID 2307220Notes

Reaction equation

HRID 2307220 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2(O)[CH2:14][N:13]([CH:15]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:12]2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].CS([Cl:33])(=O)=O>ClCCl>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2([Cl:33])[CH2:14][N:13]([CH:15]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:12]2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 536893783-(4-tert-Butylphenyl)-1-diphenylmethyl-3-azetidinol

Product 1

HCID 226054083-(4-tert-Butylphenyl)-3-chloro-1-(diphenylmethyl)azetidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of compound (9) (6.23 g) and N,Ndiisopropylethylamine (3.5 mL) in dichloromethane (100 mL) at 0° C. was added, dropwise, methanesulfonyl chloride (1.4 mL). The mixture was stired at 0° C. for 18 hrs, then washed (water, brine), dried (Na2SO4) and concentrated in vacuo. The crude product was recrystallised from hexane to give 3-(4-tert-butylphenyl)-3-chloro-1-(diphenylmethyl)azetidine (10) (4.73 g) m.p. 145° C. (hexane). Found: C, 80.30; H, 7.05; N, 3.64. C26H28CIN requires C, 80.08; H. 7.24; N, 3.59%.

Workup

  1. washwashed (water, brine)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated in vacuo
  4. customThe crude product was recrystallised from hexane

Sources & evidence

ORD record
ord-e31732783e014f3f8f46098bd2ae8628
Source dataset
uspto-grants-2004_12
Patent number
US06831078B1

Reaction notes

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