2,2,2-Trifluoroethanol → HCID 67154490, compound

HRID 83034Notes

Reaction equation

HRID 83034 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.[CH2:23](O)[C:24]([F:27])([F:26])[F:25].[C:29](=O)([O-])O.[Na+]>ClCCl>[CH:10]([N:8]1[CH2:9][CH:6]([O:5][CH2:29][CH2:23][C:24]([F:27])([F:26])[F:25])[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 64092,2,2-TrifluoroethanolHCID 516892Sodium BicarbonateHCID 27587161-(Diphenylmethyl)azetidin-3-yl methanesulfonate

Product 1

HCID 67154490HCID 67154490, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1-benzhydrylazetidin-3-yl methanesulfonate (500 mg, 1.57 mmol) in trifluoroethanol (3.5 mL, 30.7 mmol) was stirred under microwaves at 110° C. for 30 minutes. The reaction mixture was diluted by addition of dichloromethane (100 mL) and a saturated solution of sodium hydrogencarbonate (25 mL). The aqueous layer was separated and extracted with dichloromethane (2×10 mL). The combined organic phase was dried over sodium sulfate, filtered and concentrated to dryness. The residue was purified by chromatography on silica gel using dichloromethane/ethyl acetate (90:10) as eluent. The title product was obtained as a light yellow gum (170 mg, 32%).

Workup

  1. customThe aqueous layer was separated
  2. extractionextracted with dichloromethane (2×10 mL)
  3. dry with materialThe combined organic phase was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to dryness
  6. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-c93bc0096474424caa3c6571cf19ce79
Source dataset
uspto-grants-2014_09
Patent number
US08846711B2

Reaction notes

Loading…