Dichloromethane → 1-Benzhydryl-3-(4,4,4-trifluorobutoxy)-azetidine

HRID 83037Notes

Reaction equation

HRID 83037 reaction equation
CS([O:5][CH:6]1[CH2:9][N:8]([CH:10]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:7]1)(=O)=O.[F:23][C:24]([F:29])([F:28])[CH2:25][CH2:26]O.Cl[CH2:31]Cl>O>[CH:10]([N:8]1[CH2:9][CH:6]([O:5][CH2:31][CH2:26][CH2:25][C:24]([F:29])([F:28])[F:23])[CH2:7]1)([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 1375123,3,3-Trifluoro-1-propanolHCID 27587161-(Diphenylmethyl)azetidin-3-yl methanesulfonate

Product 1

HCID 671546911-Benzhydryl-3-(4,4,4-trifluorobutoxy)-azetidine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of 1-benzhydrylazetidin-3-yl methanesulfonate (247 mg, 0.78 mmol) in trifluoropropanol (1 g, 7.8 mmol) was placed under micro-wave irradiations (100 W) and heated at 100° C. during 30 minutes. The reaction mixture was diluted by addition of dichloromethane (50 mL) and water (30 mL). The two phases were separated and the aqueous phase was extracted with dichloromethane (2×20 mL). The combined organic phases were dried over sodium sulphate and concentrated to dryness. The residue was purified by chromatography on silica gel using petroleum ether/ethyl acetate (8:2) as eluent. The title product was isolated as a yellow oil (191 mg, 33%).

Workup

  1. customThe two phases were separated
  2. extractionthe aqueous phase was extracted with dichloromethane (2×20 mL)
  3. dry with materialThe combined organic phases were dried over sodium sulphate
  4. concentrationconcentrated to dryness
  5. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-3690cc64a7084b7cbf1014fa2564e15b
Source dataset
uspto-grants-2014_09
Patent number
US08846711B2

Reaction notes

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