3-Methylbenzofuran → 1-Benzhydryl-3-(3-methylbenzofuran-2-yl)azetidin-3-ol

HRID 83081ノート

反応式

HRID 83081 の反応式
[CH3:1][C:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][CH:3]=1.[Li+].CC([N-]C(C)C)C.[CH:19]([N:32]1[CH2:35][C:34](=[O:36])[CH2:33]1)([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C1COCC1>[CH:19]([N:32]1[CH2:35][C:34]([C:3]2[O:4][C:5]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=3[C:2]=2[CH3:1])([OH:36])[CH2:33]1)([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

参加物

5

反応物 3

HCID 889393-MethylbenzofuranHCID 2724682Lithium diisopropylamideHCID 37355581-(Diphenylmethyl)azetidin-3-one

生成物 1

HCID 671545491-Benzhydryl-3-(3-methylbenzofuran-2-yl)azetidin-3-ol収率 31%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of 3-methylbenzofuran (550 mg, 4.16 mmol) in dry THF (17 mL) was cooled to −78° C. and LDA (1.8 M in THF/heptane/ethylbenzene) (2.8 mL, 5.04 mmol) was added dropwise under N2 over 5 min. After stirring for 30 min, 1-benzhydrylazetidin-3-one (1.61 g, 6.78 mmol) was added portionwise over 10 min. The reaction was stirred under N2 at −78° C. for 15 min, and was then allowed to warm to rt and stirred for 1.5 h. The reaction was quenched with 0.5N HCl and extracted with EtOAc. The organic layer was washed with water and brine, dried on Na2SO4 and concentrated. The residue was purified by flash chromatography (heptane/EtOAc, 5%→35%), yielding the product (472 mg, 31%) as a yellow oil.

後処理

  1. stirringThe reaction was stirred under N2 at −78° C. for 15 min
  2. stirringstirred for 1.5 h
  3. customThe reaction was quenched with 0.5N HCl
  4. extractionextracted with EtOAc
  5. washThe organic layer was washed with water and brine
  6. customdried on Na2SO4
  7. concentrationconcentrated
  8. customThe residue was purified by flash chromatography (heptane/EtOAc, 5%→35%)

出典と根拠

ORDレコード
ord-b414ecc7b02441e3837f41fdef669830
出典データセット
uspto-grants-2014_09
特許番号
US08846711B2

反応ノート

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