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

HRID 1066063Notes

Reaction equation

HRID 1066063 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 10) (65.9 g, 275.7 mmol) in dry dichioromethane (700 ml) at 0° C. under nitrogen was added triethylamine (57 ml, 1.2 mol. equiv.). After five minutes, methanesulphonyl chloride (25.6 ml, 1.5 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 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 under reduced pressure
  5. customThe residue was chromatographed

Sources & evidence

ORD record
ord-f7bc29f657f64377ac7b9ddbbd2807fa
Source dataset
uspto-grants-2001_06
Patent number
US06242438B1

Reaction notes

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