Water → 1-(Diphenylmethyl)azetidin-3-yl methanesulfonate

HRID 1384966Notes

Reaction equation

HRID 1384966 reaction equation
[C:1]1([CH:7]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:8]2[CH2:11][CH:10]([OH:12])[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[CH3:26][S:27](Cl)(=[O:29])=[O:28].O>ClCCl>[C:13]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[N:8]2[CH2:11][CH:10]([O:12][S:27]([CH3:26])(=[O:29])=[O:28])[CH2:9]2)[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 3304481-(Diphenylmethyl)azetidin-3-ol

Product 1

HCID 27587161-(Diphenylmethyl)azetidin-3-yl methanesulfonateYield 83.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-diphenylmethylazetidin-3-ol (see Preparation 3(a)) (65.9 g, 275.7 mmol) in dry dichloromethane (700 ml) at 0° C. under nitrogen was added triethylamine (57 ml, 1.5 mol. equiv.). After five minutes, methanesulphonyl chloride (25.6 ml, 1.2 mol. equiv.) was added and the mixture stirred for one hour. Water (300 ml) was then added and the mixture extracted with dichloromethane (3×300 ml). The combined organic layers were dried over magnesium sulphate. The solution was then filtered and the solvent removed from the filtrate by evaporation under reduced pressure. The residue was chromatographed using silica gel eluting with methanol:dichloromethane (1:49, by volume) to give the title compound (73.4 g) as a solid.

Workup

  1. extractionthe mixture extracted with dichloromethane (3×300 ml)
  2. dry with materialThe combined organic layers were dried over magnesium sulphate
  3. filtrationThe solution was then filtered
  4. customthe solvent removed from the filtrate by evaporation under reduced pressure
  5. customThe residue was chromatographed

Sources & evidence

ORD record
ord-f42bed0d1bd74d9e910bcc9509be0637
Source dataset
uspto-grants-2001_07
Patent number
US06262075B1

Reaction notes

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