4-Methylmorpholine → 1-(Diphenylmethyl)azetidin-3-one

HRID 605701

反応式

HRID 605701 の反応式
Cl.[C:2]1([CH:8]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:9]2[CH2:12][CH:11]([OH:13])[CH2:10]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN1CCOCC1.C[N+]1([O-])CCOCC1.C(OCC)(=O)C>ClCCl.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[C:14]1([CH:8]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[N:9]2[CH2:12][C:11](=[O:13])[CH2:10]2)[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

参加物

7

反応物 4

HCID 79724-MethylmorpholineHCID 8857Ethyl AcetateHCID 82029Methyl morpholine oxideHCID 28017261-benzhydrylazetidin-3-ol Hydrochloride

生成物 1

HCID 37355581-(Diphenylmethyl)azetidin-3-one収率 37%

試薬・触媒・溶媒 2

HCID 178419074HCID 178419074、化合物触媒HCID 6344Dichloromethane溶媒

実験手順

1-(Diphenylmethyl)azetidin-3-ol hydrochloride (2.75 g, 9.98 mmol), prepared using procedures similar to those described for Scheme 1 of the General Synthetic Section, 3 Å molecular sieves and 4-methylmorpholine (1.1 mL, 10.0 mmol) were suspended in dichloromethane (20 mL) at 0° C. 4-Methylmorpholine N-oxide (2.93 g, 25.0 mmol) and tetrapropylammonium perruthenate (140 mg, 0.399 mmol) were added and the mixture was stirred at ambient for 24 h. The mixture was filtered through a plug of silica using 5% triethylamine in ethyl acetate as eluent. The filtrate was concentrated in vacuo and the residue was partitioned between ethyl acetate and saturated sodium bicarbonate solution. The organic portion was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. Column chromatography (silica gel, 8:1 hexanes:ethyl acetate) gave 1-(diphenylmethyl)azetidin-3-one (871 mg, 3.68 mmol, 37% yield): 1H NMR (400 MHz, CDCl3): 7.50-7.46 (m, 4H), 7.33-7.27 (m, 4H), 7.27-7.19 (m, 2H), 4.59 (s, 1H), 4.01 (s, 4H); MS (EI) for C16H15NO: 238 (MH+).

後処理

  1. filtrationThe mixture was filtered through a plug of silica using 5% triethylamine in ethyl acetate as eluent
  2. concentrationThe filtrate was concentrated in vacuo
  3. customthe residue was partitioned between ethyl acetate and saturated sodium bicarbonate solution
  4. washThe organic portion was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-38235d1b3823428da89e2cee2812fd2e
出典データセット
uspto-grants-2011_03
特許番号
US07915250B2

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