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

HRID 1457088Notes

Reaction equation

HRID 1457088 reaction equation
C(N(CC)CC)C.[C:8]1([CH:14]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:15]2[CH2:18][CH:17]([OH:19])[CH2:16]2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH3:26][S:27](Cl)(=[O:29])=[O:28].O>ClCCl>[C:20]1([CH:14]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:15]2[CH2:18][CH:17]([O:19][S:27]([CH3:26])(=[O:29])=[O:28])[CH2:16]2)[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=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

Triethylamine (57 ml, 1.5 mol equivalent) was added to a solution of 1-diphenylmethylazetidin-3-ol (65.9 g, 275.7 mmol) in dry dichloromethane (700 ml) at 0° C. under nitrogen. After five minutes, methanesulphonyl chloride (25.6 ml, 1.2 mol equivalent) was added and the mixture stirred for one hour. Water (300 ml) was added and the mixture extracted with dichloromethane (3×300 ml). The combined organic layers were dried over magnesium sulphate and the solvent removed under reduced pressure. The residue was chromatographed on silica gel eluting with methanol:dichloromethane (1.49, by volume) to give the title product (73.4 g) as a solid. 1H-NMR (CDCl3): δ=2.95(s,3H), 3.15-3.25(m,2H), 3.6-3.65(m,2H), 4.4(s,1H), 5.05-5.15(m,1H), 7.15-7.4(m,10H)ppm.

Workup

  1. extractionthe mixture extracted with dichloromethane (3×300 ml)
  2. dry with materialThe combined organic layers were dried over magnesium sulphate
  3. customthe solvent removed under reduced pressure
  4. customThe residue was chromatographed on silica gel eluting with methanol

Sources & evidence

ORD record
ord-5c9eb5c9803a48fe98baeb02e3c90bcc
Source dataset
uspto-grants-1998_12
Patent number
US05846965

Reaction notes

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