4-Toluenesulfonyl chloride → 1-Benzhydryl-3-(toluene-4-sulfonyl)-azetidine

HRID 1177415Notes

Reaction equation

HRID 1177415 reaction equation
[CH:1]([N:14]1[CH2:17][CH:16](O)[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.[C:19]1([CH3:29])[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1>N1C=CC=CC=1.CN(C1C=CN=CC=1)C>[CH:1]([N:14]1[CH2:17][CH:16]([S:25]([C:22]2[CH:23]=[CH:24][C:19]([CH3:29])=[CH:20][CH:21]=2)(=[O:27])=[O:26])[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

Participants

5

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 3304481-(Diphenylmethyl)azetidin-3-ol

Product 1

HCID 671126111-Benzhydryl-3-(toluene-4-sulfonyl)-azetidine

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

To a solution of 1-benzhydrylazetidin-3-ol (20 g, 0.835 mol) in pyridine (167 mL) was added DMAP (12.24 g, 0.1 mM) and p-toluene sulphonylchloride at −40° C. The reaction mixture was stirred overnight. The reaction mixture was partitioned between dichloromethane (200 mL) and water. Solvent was evaporated off, purified by column chromatography using silica gel, 100-200 mesh) and 10% ethyl acetate hexane as eluent to obtain 1-benzhydryl-3-(toluene-4-sulfonyl)-azetidine. 1H-NMR (400 MHz, CDCl3,), δ ppm 7.76-7.74 (m, 2H), 7.34-7.15 (m, 12H), 4.89-4.85 (m, 1H), 4.32 (s, 1H), 3.47-3.43 (m, 2H), 3.06-3.03 (m, 2H), 2.43 (s, 3H).

Workup

  1. customThe reaction mixture was partitioned between dichloromethane (200 mL) and water
  2. customSolvent was evaporated off
  3. custompurified by column chromatography

Sources & evidence

ORD record
ord-4b88c8a47bdd43e090ef450711d5d336
Source dataset
uspto-grants-2010_11
Patent number
US07842685B2

Reaction notes

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