Methanesulfonyl chloride → HCID 22605405, compound

HRID 2307222Notes

Reaction equation

HRID 2307222 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2(O)[CH2:11][N:10]([CH:12]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:9]2)=[CH:4][CH:3]=1.C(N(CC)C(C)C)(C)C.CS([Cl:39])(=O)=O>ClCCl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([Cl:39])[CH2:11][N:10]([CH:12]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 53767266HCID 53767266, compound

Product 1

HCID 22605405HCID 22605405, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 3-(4-fluorophenyl)-1-diphenylmethyl-3-azetidinol (15) (4.0 g) and N,N-diisopropylethylamine (3.2 mL) in dichloromethane (100 mL) at 0° C. was added, dropwise, methanesulfonyl chloride (125 mL). The mixture was stirred at 0° C. for 18 hrs, then washed (water, brine) and dried (Na2SO4) and concentrated in vacuo. The crude product was recrystallised from hexane to give 3-(4-fluorophenyl)-3-chloro-1-(diphenylmethyl)azetidine (16) (22 g), m.p. 108-109° C. (hexane). Found: C, 75.13; H, 5.46; N, 3.93. C22H19CIFN C, 75.10; H, 5.44; N, 3.98%.

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-bafba58ab5c640f4b9df5d0192c1a98e
Source dataset
uspto-grants-2004_12
Patent number
US06831078B1

Reaction notes

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