Triethylamine → 1-(Diphenylmethyl)azetidin-3-one

HRID 865701Notes

Reaction equation

HRID 865701 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>CS(C)=O>[C:20]1([CH:14]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:15]2[CH2:18][C:17](=[O:19])[CH2:16]2)[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 3304481-(Diphenylmethyl)azetidin-3-ol

Product 1

HCID 37355581-(Diphenylmethyl)azetidin-3-oneYield 98.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Conditions

Temperature
10 °C

Procedure

Triethylamine (112.1 g, 1.11 mol) was added to a solution of N-diphenylmethylazetidin-3-ol (26.6 g, 0.11 mol) in DMSO (300 ml). The solution was cooled to 10° C. and a solution of sulphur trioxide-pyridine complex (112 g, 0.7 mol) in DMSO (500 ml) added, rapidly. Stirring was continued at 10° C. for 0.75 h and the mixture then warmed to 25° C. and stirred for 1 h. The solution was poured into ice-water (21) and extracted with EtOAc (3×1l). The combined extracts were washed with water (500 ml) and brine (500 ml) and dried (Na2SO4). The crude product was purified by chromatography through silica-gel eluting with petroleum ether/EtOAc (2:1) to give the desired ketone (25.8 g), mp 74°-75° C. δ (360 MHz, CDCl3) 4.00 (4H, s, 2 of CH2), 4.59 (1H, s, CH), 7.19-7.49 (10H, m, Ar--H).

Workup

  1. temperaturethe mixture then warmed to 25° C.
  2. stirringstirred for 1 h
  3. extractionextracted with EtOAc (3×1l)
  4. washThe combined extracts were washed with water (500 ml) and brine (500 ml)
  5. dry with materialdried (Na2SO4)
  6. customThe crude product was purified by chromatography through silica-gel
  7. washeluting with petroleum ether/EtOAc (2:1)

Sources & evidence

ORD record
ord-7a1a486ccac74e9098dffb3001b35387
Source dataset
uspto-grants-1996_10
Patent number
US05567726

Reaction notes

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