Triethylamine → 1-Benzhydryl-3-(benzofuran-2-yl)azetidine

HRID 2172118Notes

Reaction equation

HRID 2172118 reaction equation
[CH:1]([N:14]1[CH2:17][C:16]([C:19]2[O:20][C:21]3[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=3[CH:23]=2)(Cl)[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(N(CC)CC)C>[Pd].C(OCC)(=O)C.C(O)C>[CH:1]([N:14]1[CH2:17][CH:16]([C:19]2[O:20][C:21]3[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=3[CH:23]=2)[CH2:15]1)([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 2

HCID 8471TriethylamineHCID 67154605HCID 67154605, compound

Product 1

HCID 671547231-Benzhydryl-3-(benzofuran-2-yl)azetidine

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalyst2×HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1-benzhydryl-3-(benzofuran-2-yl)-3-chloroazetidine (458 mg, 1.23 mmol) and 10% palladium on carbon (130 mg) in ethyl acetate (6 mL) and ethanol (6 mL) was stirred at room temperature under hydrogen atmosphere (˜1 atm) for 1 day. An additional amount of 10% palladium on carbon (130 mg) was added as well as triethylamine (171 μL, 1.23 mmol) and hydrogenation was continued under same conditions for 3 days. After removal of hydrogen, the mixture was diluted with dichloromethane (50 mL), filtered through Clarcel® and concentrated. The residue was taken up in dichloromethane (30 mL) and washed with aqueous saturated sodium hydrogencarbonate (30 mL). The aqueous layer was back-washed with dichloromethane (2×30 mL) and all the combined organic layers were dried over sodium sulfate, filtered and concentrated. The residue was purified by chromatography on silica gel using petroleum ether/ethyl acetate (100:0 to 95:5) as eluent. The title compound was obtained as a yellow gum (111 mg, 27%).

Workup

  1. waitwas continued under same conditions for 3 days
  2. customAfter removal of hydrogen
  3. additionthe mixture was diluted with dichloromethane (50 mL)
  4. filtrationfiltered through Clarcel®
  5. concentrationconcentrated
  6. washwashed with aqueous saturated sodium hydrogencarbonate (30 mL)
  7. washThe aqueous layer was back-washed with dichloromethane (2×30 mL) and all the combined organic layers
  8. dry with materialwere dried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-85e791c1f5b34f44b152ac7b43204d4f
Source dataset
uspto-grants-2015_06
Patent number
US09051321B2

Reaction notes

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