Trifluoroacetic acid → 1-Benzhydryl-3-(3-methylbenzofuran-2-yl)azetidine

HRID 2172134Notes

Reaction equation

HRID 2172134 reaction equation
[CH:1]([N:14]1[CH2:17][C:16]([C:19]2[O:20][C:21]3[CH:28]=[CH:27][CH:26]=[CH:25][C:22]=3[C:23]=2[CH3:24])(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.C([SiH](CC)CC)C.FC(F)(F)C(O)=O.B(F)(F)F.CCOCC>ClCCl>[CH:1]([N:14]1[CH2:17][CH:16]([C:19]2[O:20][C:21]3[CH:28]=[CH:27][CH:26]=[CH:25][C:22]=3[C:23]=2[CH3:24])[CH2:15]1)([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 8000Boron trifluoride etherateHCID 12052TriethylsilaneHCID 671545491-Benzhydryl-3-(3-methylbenzofuran-2-yl)azetidin-3-ol

Product 1

HCID 671546541-Benzhydryl-3-(3-methylbenzofuran-2-yl)azetidineYield 63%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cooled (0° C.) solution of 1-benzhydryl-3-(3-methylbenzofuran-2-yl)azetidin-3-ol (406 mg, 1.099 mmol) in dichloromethane (50 mL) were added triethylsilane (1.775 mL, 10.99 mmol) and trifluoroacetic acid (1.630 mL, 22.01 mmol). The reaction mixture was warmed to rt and stirred for 23 h. After 18 h, boron trifluoride etherate (0.6 mL, 4.73 mmol) was added and the reaction was allowed to stir for an additional 5 h. The reaction mixture was partitioned between sat. NaHCO3 and DCM. The layers were separated, the organic layer was washed with sat. NaHCO3 and brine, dried on Na2SO4 and concentrated. The residue was purified by flash chromatography (heptane/EtOAc, 0%→30%), yielding the title product (244 mg, 63%) as an off-white solid.

Workup

  1. waitAfter 18 h
  2. stirringto stir for an additional 5 h
  3. customThe reaction mixture was partitioned between sat. NaHCO3 and DCM
  4. customThe layers were separated
  5. washthe organic layer was washed with sat. NaHCO3 and brine
  6. customdried on Na2SO4
  7. concentrationconcentrated
  8. customThe residue was purified by flash chromatography (heptane/EtOAc, 0%→30%)

Sources & evidence

ORD record
ord-20ecc5c4590b470bac792026e7857963
Source dataset
uspto-grants-2015_06
Patent number
US09051321B2

Reaction notes

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