Water → HCID 19005929, compound

HRID 1742996Notes

Reaction equation

HRID 1742996 reaction equation
[CH:1]([N:14]1[CH2:17][CH:16](OS(C)(=O)=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.[K].[NH:24]1[CH:28]=[N:27][C-:26]=[N:25]1.O>CN(C)C=O>[CH:1]([N:14]1[CH2:17][CH:16]([N:24]2[CH:28]=[N:27][CH:26]=[N:25]2)[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 3

HCID 962WaterHCID 27587161-(Diphenylmethyl)azetidin-3-yl methanesulfonateHCID 131718653HCID 131718653, compound

Product 1

HCID 19005929HCID 19005929, compoundYield 68.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of N-benzhydryl-3-[(methylsulfonyl)oxy]azetidine (0. 951 g, 3 mmol) and potassium-1,2,4-triazolide (0.69 g, 6.5 mmol) in 50 ml of dimethylformamide was heated at 85°-90° C. overnight. To this, water (200 ml) was added and extracted with ethyl acetate. The combined organic layers were washed with water, dried (Na2SO4) and evaporated to yield 0.9 g of the crude which upon purification over silica gel using ethyl acetate as solvent yielded 0.6 g of the desired product as a white solid. 1H NMR (CDCl3) δ: 8.22 (s, 1H), 7.97 (s, 1H), 7.57-7.12 (m, 5H), 5.13-4.9 (m, 1H), 4.53 (s, 1H), 3.8-3.4 (m, 4H).

Workup

  1. temperaturewas heated at 85°-90° C. overnight
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layers were washed with water
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. customto yield 0.9 g of the crude which
  7. customupon purification over silica gel

Sources & evidence

ORD record
ord-c313ba9b6a0d4334a278a0f18fa851a5
Source dataset
uspto-grants-1994_08
Patent number
US05342846

Reaction notes

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