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

HRID 634017ノート

反応式

HRID 634017 の反応式
[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

参加物

6

反応物 2

HCID 8471TriethylamineHCID 67154605HCID 67154605、化合物

生成物 1

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

試薬・触媒・溶媒 3

HCID 23938Palladium触媒2 回HCID 702Ethanol溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-6eaa5502abbe477080442fa34268d744
出典データセット
uspto-grants-2016_04
特許番号
US09321769B2

反応ノート

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